TW201422568A - 磷光oled及磷光oled電洞傳輸材料 - Google Patents
磷光oled及磷光oled電洞傳輸材料 Download PDFInfo
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- TW201422568A TW201422568A TW102137587A TW102137587A TW201422568A TW 201422568 A TW201422568 A TW 201422568A TW 102137587 A TW102137587 A TW 102137587A TW 102137587 A TW102137587 A TW 102137587A TW 201422568 A TW201422568 A TW 201422568A
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- cycloalkyl
- alkoxy
- alkyl
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- 239000000463 material Substances 0.000 title description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- -1 C3-C20 cycloalkyl Chemical group 0.000 claims description 41
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 17
- 230000000903 blocking effect Effects 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000004888 barrier function Effects 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 3
- 230000005540 biological transmission Effects 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 13
- 239000011159 matrix material Substances 0.000 abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 96
- 239000010410 layer Substances 0.000 description 64
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 50
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 24
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 16
- 230000005525 hole transport Effects 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- KSCGBFWJQRWORE-UHFFFAOYSA-N n-(4-tert-butylphenyl)-4-phenylaniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C=2C=CC=CC=2)C=C1 KSCGBFWJQRWORE-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 9
- 239000002800 charge carrier Substances 0.000 description 9
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- DPKKOVGCHDUSAI-UHFFFAOYSA-N 1,3-dibromo-5-methylbenzene Chemical compound CC1=CC(Br)=CC(Br)=C1 DPKKOVGCHDUSAI-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- LKQYEULDFDVLLZ-UHFFFAOYSA-N 3,5-dimethyl-n-(4-phenylphenyl)aniline Chemical compound CC1=CC(C)=CC(NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 LKQYEULDFDVLLZ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- CXIUCDYMMHBFFJ-UHFFFAOYSA-N 1,3-dibromo-5-(3,5-dimethylphenyl)benzene Chemical group CC1=CC(C)=CC(C=2C=C(Br)C=C(Br)C=2)=C1 CXIUCDYMMHBFFJ-UHFFFAOYSA-N 0.000 description 3
- HIHYAKDOWUFGBK-UHFFFAOYSA-N 1,3-dibromo-5-phenylbenzene Chemical group BrC1=CC(Br)=CC(C=2C=CC=CC=2)=C1 HIHYAKDOWUFGBK-UHFFFAOYSA-N 0.000 description 3
- GRMLGYULZHLWRH-UHFFFAOYSA-N 1-bromo-3-(3-bromo-5-methylphenyl)-5-methylbenzene Chemical group CC1=CC(Br)=CC(C=2C=C(Br)C=C(C)C=2)=C1 GRMLGYULZHLWRH-UHFFFAOYSA-N 0.000 description 3
- WXAXPKLHPBZXSN-UHFFFAOYSA-N CC(=NC1=CC=C(C=C1)C2=CC=CC=C2)C Chemical compound CC(=NC1=CC=C(C=C1)C2=CC=CC=C2)C WXAXPKLHPBZXSN-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 2
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 2
- MOEQCTRZXSMAJC-UHFFFAOYSA-N 1-n,3-n,5-tris(3,5-dimethylphenyl)-1-n,3-n-bis(4-phenylphenyl)benzene-1,3-diamine Chemical compound CC1=CC(C)=CC(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=C(C=C(C=2)N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 MOEQCTRZXSMAJC-UHFFFAOYSA-N 0.000 description 2
- OBRJFKHFZNQXNA-UHFFFAOYSA-N 1-n,3-n-bis(3,5-dimethylphenyl)-1-n,3-n-bis(4-phenylphenyl)benzene-1,3-diamine Chemical compound CC1=CC(C)=CC(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=C(C=CC=2)N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=C(C)C=C(C)C=2)=C1 OBRJFKHFZNQXNA-UHFFFAOYSA-N 0.000 description 2
- CEJOOPSMWHGNAR-UHFFFAOYSA-N 1-n,3-n-bis(3,5-dimethylphenyl)-5-methyl-1-n,3-n-bis(4-phenylphenyl)benzene-1,3-diamine Chemical compound CC1=CC(C)=CC(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=C(C=C(C)C=2)N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=C(C)C=C(C)C=2)=C1 CEJOOPSMWHGNAR-UHFFFAOYSA-N 0.000 description 2
- IUQJCDYVXSPRHG-UHFFFAOYSA-N 1-n,3-n-bis(3,5-dimethylphenyl)-5-phenyl-1-n,3-n-bis(4-phenylphenyl)benzene-1,3-diamine Chemical compound CC1=CC(C)=CC(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=C(C=C(C=2)N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=C(C)C=C(C)C=2)C=2C=CC=CC=2)=C1 IUQJCDYVXSPRHG-UHFFFAOYSA-N 0.000 description 2
- AEFLFWKHWAQSDV-UHFFFAOYSA-N 1-n,3-n-bis(4-tert-butylphenyl)-1-n,3-n-bis(4-phenylphenyl)-5-[3-(trifluoromethyl)phenyl]benzene-1,3-diamine Chemical compound C1=CC(C(C)(C)C)=CC=C1N(C=1C=C(C=C(C=1)N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)C(C)(C)C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=C(C=2C=CC=CC=2)C=C1 AEFLFWKHWAQSDV-UHFFFAOYSA-N 0.000 description 2
- NKCRWXOHIPXOCI-UHFFFAOYSA-N 1-n,3-n-bis(4-tert-butylphenyl)-1-n,3-n-bis(4-phenylphenyl)-5-pyridin-3-ylbenzene-1,3-diamine Chemical compound C1=CC(C(C)(C)C)=CC=C1N(C=1C=C(C=C(C=1)N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)C(C)(C)C)C=1C=NC=CC=1)C1=CC=C(C=2C=CC=CC=2)C=C1 NKCRWXOHIPXOCI-UHFFFAOYSA-N 0.000 description 2
- KHEJWXFQBXMJJL-UHFFFAOYSA-N 1-n,3-n-bis(4-tert-butylphenyl)-1-n,3-n-bis(4-phenylphenyl)benzene-1,3-diamine Chemical compound C1=CC(C(C)(C)C)=CC=C1N(C=1C=C(C=CC=1)N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)C(C)(C)C)C1=CC=C(C=2C=CC=CC=2)C=C1 KHEJWXFQBXMJJL-UHFFFAOYSA-N 0.000 description 2
- VBILEDDKKLTPLQ-UHFFFAOYSA-N 1-n,3-n-bis(4-tert-butylphenyl)-5-(3,5-dimethylphenyl)-1-n,3-n-bis(4-phenylphenyl)benzene-1,3-diamine Chemical compound CC1=CC(C)=CC(C=2C=C(C=C(C=2)N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C(C)(C)C)N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C(C)(C)C)=C1 VBILEDDKKLTPLQ-UHFFFAOYSA-N 0.000 description 2
- UAIULUJFIQWGEH-UHFFFAOYSA-N 1-n,3-n-bis(4-tert-butylphenyl)-5-methyl-1-n,3-n-bis(4-phenylphenyl)benzene-1,3-diamine Chemical compound C=1C(C)=CC(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C(C)(C)C)=CC=1N(C=1C=CC(=CC=1)C(C)(C)C)C(C=C1)=CC=C1C1=CC=CC=C1 UAIULUJFIQWGEH-UHFFFAOYSA-N 0.000 description 2
- GXIVGJPUFZTSEG-UHFFFAOYSA-N 1-n,3-n-bis(4-tert-butylphenyl)-5-phenyl-1-n,3-n-bis(4-phenylphenyl)benzene-1,3-diamine Chemical compound C1=CC(C(C)(C)C)=CC=C1N(C=1C=C(C=C(C=1)N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)C(C)(C)C)C=1C=CC=CC=1)C1=CC=C(C=2C=CC=CC=2)C=C1 GXIVGJPUFZTSEG-UHFFFAOYSA-N 0.000 description 2
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 2
- OAEPBDRGXUPMAA-UHFFFAOYSA-N 5-methyl-1-n,3-n-bis(4-methylphenyl)-1-n,3-n-bis(4-phenylphenyl)benzene-1,3-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(C=C(C)C=1)N(C=1C=CC(C)=CC=1)C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(C=2C=CC=CC=2)C=C1 OAEPBDRGXUPMAA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- DJGHSJBYKIQHIK-UHFFFAOYSA-N (3,5-dimethylphenyl)boronic acid Chemical compound CC1=CC(C)=CC(B(O)O)=C1 DJGHSJBYKIQHIK-UHFFFAOYSA-N 0.000 description 1
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- BLWZWNFGLGRLLJ-UHFFFAOYSA-N 1,3-dibromo-5-[3-(trifluoromethyl)phenyl]benzene Chemical group FC(F)(F)C1=CC=CC(C=2C=C(Br)C=C(Br)C=2)=C1 BLWZWNFGLGRLLJ-UHFFFAOYSA-N 0.000 description 1
- OQZAQBGJENJMHT-UHFFFAOYSA-N 1,3-dibromo-5-methoxybenzene Chemical compound COC1=CC(Br)=CC(Br)=C1 OQZAQBGJENJMHT-UHFFFAOYSA-N 0.000 description 1
- FXUNKKHKRBPXAE-UHFFFAOYSA-N 1-bromo-3-(3-bromo-5-methoxyphenyl)-5-methoxybenzene Chemical group COC1=CC(Br)=CC(C=2C=C(OC)C=C(Br)C=2)=C1 FXUNKKHKRBPXAE-UHFFFAOYSA-N 0.000 description 1
- LPLLWKZDMKTEMV-UHFFFAOYSA-N 1-bromo-3-(3-bromophenyl)benzene Chemical group BrC1=CC=CC(C=2C=C(Br)C=CC=2)=C1 LPLLWKZDMKTEMV-UHFFFAOYSA-N 0.000 description 1
- BDOOZZQGKBKQCH-UHFFFAOYSA-N 3-(3,5-dibromophenyl)pyridine Chemical compound BrC1=CC(Br)=CC(C=2C=NC=CC=2)=C1 BDOOZZQGKBKQCH-UHFFFAOYSA-N 0.000 description 1
- LVTFSVIRYMXRSR-WUKNDPDISA-N 3-methyl-4'-dimethylaminoazobenzene Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC(C)=C1 LVTFSVIRYMXRSR-WUKNDPDISA-N 0.000 description 1
- CWVPIIWMONJVGG-UHFFFAOYSA-N 3-methyl-n-(3-methylphenyl)aniline Chemical compound CC1=CC=CC(NC=2C=C(C)C=CC=2)=C1 CWVPIIWMONJVGG-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
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- ASLPULHXNPKGRJ-UHFFFAOYSA-N 5-methyl-1-n,3-n-bis(4-methylphenyl)-1-n,3-n-dinaphthalen-2-ylbenzene-1,3-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(C=C(C)C=1)N(C=1C=CC(C)=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=CC=C2)C2=C1 ASLPULHXNPKGRJ-UHFFFAOYSA-N 0.000 description 1
- ZFICTELOKRFUNH-UHFFFAOYSA-N 5-methyl-1-n,3-n-dinaphthalen-1-yl-1-n,3-n-diphenylbenzene-1,3-diamine Chemical compound C=1C(C)=CC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)=CC=1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 ZFICTELOKRFUNH-UHFFFAOYSA-N 0.000 description 1
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- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- WOAORAPRPVIATR-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C(F)(F)F)=C1 WOAORAPRPVIATR-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
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- 239000003480 eluent Substances 0.000 description 1
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- 230000001747 exhibiting effect Effects 0.000 description 1
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- IBJHDUPUTZQCLL-UHFFFAOYSA-N n-(4-methylphenyl)naphthalen-2-amine Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C=CC=C2)C2=C1 IBJHDUPUTZQCLL-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
本發明有關於磷光有機發光二極管(OLED),該磷光有機發光二極管(OLED)包含電洞傳輸或電洞傳輸以及電子阻擋層,該電子阻擋層包含N,N,N’,N’-四芳基-亞苯基-3,5-二胺或N,N,N’,N’-四芳基-1,1’-聯苯-3,3’-二胺基質化合物,以及有關於有用於作為磷光OLED中電洞傳輸以及電子阻擋層基質的新的N,N,N’,N’-四芳基取代的m-亞芳基二胺化合物。
Description
本發明有關磷光有機發光裝置,以及有關可在這種裝置中使用的化合物,尤其是在其電洞傳輸及/或電子阻擋層中使用。
在OLED中,使用了某些有機材料的電發光(EL)特徵。在EL裝置中,電壓的應用創造出了適合的電荷載體,其如果重新結合的話,形成了活化的狀態,其藉由發光回到基本狀態。對了改進效率,有機發光二極管在發光層之間也很常具有電荷傳輸層,其負責將負與正電荷載體傳輸至該發光層中。取決於所傳輸的電荷載體,將這些電荷傳輸層分類成電洞導體以及電子導體。已知一種用於光伏裝置的相當類似的層組,例如有機太陽能電池。可藉由已知的方法來產生具有數層的有機半導體裝置,例如在真空下蒸發或從溶液沉積。
換言之,在有機發光二極管的例子中,由於外部施加的電壓,隨之在活性區形成激子(電子-電洞對),以及這些激子的輻射復合,藉由電荷載體(來自一側的電子、來自另一側的電洞)從接點注入至鄰近的有機層來產生並發出光。
在第1圖上示意性地描繪了具有鄰近基板的正極(陰極)的最常見OLED結構,其中數字1-9代表了下述層: 1. 基板 2. 基極,電洞注入(正極),通常是透明的 3. 電洞注入層 4. 電洞傳輸層(HTL) 5. 發光層(EL) 6. 電子傳輸層(ETL) 7. 電子注入層 8. 加罩電極(通常是具有低功函數、電子注入的金屬(負極)) 9. 封裝,以隔離環境影響。
雖然前述代表了最典型的例子,常常可省略數層,或可結合一層用於數個特性。
有機半導體材料的一個重要特性是它們的傳導性。薄層樣本的傳導性可藉由,例如,所謂的兩點法來測量。在此,將電壓施加至該薄層,並測量流經該層的電流。藉由考慮接點的幾何學以及樣本層的厚度來產生所測量的電阻、各自的傳導性。
在OLED中,不僅由特定層的電阻以及厚度給出了操作電壓(或更確切而言,整體的電阻),也由用於將電荷載體從特定層注入至鄰近層的能量障礙來給出。裝置的功率效率(在給定波長下或在給定顏色範圍中的光通量中的電功率轉換)取決於由整體電阻所給定的焦耳損失以及光子中的電荷載體的轉換效率,其取決於電荷載體(電子-電洞)平衡以及該裝置中所形成的電子-電洞對(激子)的輻射復合的量子效率。
有穩定的努力以發展材料以及OLED設計,其允許最小化焦耳損失,確保電荷載體平衡,並最大化量子效率。在最小化焦耳損失中,顯著的改進導致特殊電荷注入層的設計以及電摻雜電荷傳輸層的採用。特定的電荷注入以及阻擋層也可改進電荷載體平衡。在量子效率中最重要的改進導致磷光射極的採用,其允許了不僅利用單態激子,也利用三重態激子狀態,其在正常情況下在激子總體中在統計上是普遍的。
在先前技術中,用於製備電洞傳輸層及/或電子/激子阻擋層的若干材料是已知的。
然而,由於先前的材料以及設計發展,儘管在OLED性能中達成了令人欽佩的結果,OLED效率仍顯著地低於其理論限制,且許多其他的OLED性能參數(像是光度以及壽命)也可被進一步改進。
因此本發明的一個目的是提供改進的磷光OLED,該改進的磷光OLED比起根據現有技術使用電洞傳輸以及電子阻擋基質的裝置具有較低的操作電壓及/或較高的效率。本發明的另一個目的是提供新的化合物,其可用以作為用於電洞傳輸層及/或電子/激子阻擋層的基質材料,其克服了先前技術的缺點並且尤其可在磷光OLED中使用。
此目的藉由在陽極以及陰極之間包含至少一發光層的OLED來達成,該至少一發光層包含磷光射極以及至少一電洞傳輸層,該至少一電洞傳輸層包含由通式(I)表示的化合物其中R1-R20可獨立地選自氫、C1-C20烷基或C3-C20環烷基、C1-C20烷氧基或C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基, i)R1-R5的至少其中之一以及R11-R15的至少其中之一是C6-C20芳基或C2-C20雜芳基,或 ii)R1與R2以及R11與R12形成芳香環,或 iii)R2與R3以及R12與R13形成芳香環; R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基 以及 x是選自0以及1的整數,其中對於x=0,R22具有與R1-R20相同的意義,而對於x=1,R21以及R22獨立地選自氫、C1-C10烷基、C3-C10環烷基、C1-C10烷氧基以及C3-C10環烷基氧基。該烷基或烷氧基取代基可為飽和或不飽和的、直鏈或分支的。該環烷基或環烷氧基取代基可為飽和或不飽和的、單環或多環的。在取代基的整體C原子數包括可能的烷基取代、分支及/或該取代基內環狀結構的發生。如果該雜芳基取代基是經由碳環或經由含有上至三個雜原子(獨立地選自O、N以及S)的五元雜環來附接,那就是有利的。較佳的是,在化合物(I)中的整體C原子數不超過150。更佳的是,在選自R1-R5、R6-R10、R11-R15、R16-R20的取代基的任何基團中的整體C原子數,也就是鍵結至在結構(I)中鍵結至氮原子的其中一個苯基環的所有取代基,不超過20。最佳的是,在選自R1-R5、R6-R10、R11-R15、R16-R20的取代基的任何基團中的整體C原子數不超過12。
在一個較佳具體實施例中,R1-R5的至少其中之一以及R11-R15的至少其中之一是C6-C20芳基或C2-C20雜芳基,而其他的R1-R5以及R11-R15是氫。在一個更佳的具體實施例中,R1-R5的至少其中之一以及R11-R15的至少其中之一是苯基,而其他的R1-R5以及R11-R15是氫。在另一個較佳具體實施例中,R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基。在更佳的具體實施例中,R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基,而其他的R6-R10以及R16-R20是氫。在一個甚至較佳的具體實施例中,R3以及R13是苯基,以及在具有苯基環的R3以及R13上的其他取代基是氫原子。在另一個較佳的具體實施例中,R1-R5與R11-R15相同,以及R6-R10與R16-R20相同。在更另一個較佳具體實施例中,R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C12烷基、C3-C12環烷基。更佳的是,R8以及R18是叔丁基,或R7、R9、R17以及R19是甲基。對於x=1,R21以及R22較佳獨立地選自甲基或甲氧基。更佳的是,R21以及R22是相同的。較佳的也是上述較佳具體實施例的所有可能組合。
更佳的是包含由通式(II)或(III)表示的一般結構(I)的具體實施例的裝置 其中Ar以及Ar1是選自4-叔丁基苯基、3,5-二甲基苯基以及2,4,6-三甲基苯基、R23具有與上面定義的R22相同的意義,以及R24是氫、C1-C10烷基、C3-C10環烷基、C1-C10烷氧基以及C3-C10環烷基氧基。
較佳的是,R23是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基。更佳的是,R23是選自甲基、苯基、3,5-二甲基苯基以及1,1’-二苯基-4-基所組成的群組。較佳的是,R24是C1-C4烷基或C1-C4烷氧基。【】更佳的是,R24是選自甲基以及甲氧基。
進一步的目的是由如上面定義的通式(I)的新化合物來達成,其中 i)R1-R5的至少其中之一以及R11-R15的至少其中之一是C6-C20芳基或C2-C20雜芳基,或 ii)R1與R2以及R11與R12形成芳香環,或 iii)R2與R3以及R12與R13形成芳香環; R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基 以及 x是選自0以及1的整數,其中對於x=0,R22具有與R1-R20相同的意義,而對於x=1,R21以及R22獨立地選自氫、C1-C10烷基、C3-C10環烷基、C1-C10烷氧基以及C3-C10環烷基氧基。
烷基或烷氧基取代基可為飽和或不飽和的、直鏈或分支的。環烷基或環烷氧基取代基可為飽和或不飽和的、單環或多環的。取代基中的整體C原子數包括可能的烷基取代、分支及/或該取代基內環狀結構的發生。如果該雜芳基取代基是經由碳環或經由含有上至三個雜原子(獨立地選自O、N以及S)的五元雜環附接,那麼就是有利的。較佳的是,化合物(I)中的整體C原子數不超過150。更佳的是,在選自R1-R5、R6-R10、R11-R15、R16-R20的取代基的任何基團中的整體C原子數,也就是鍵結至在結構(I)中鍵結至氮原子的其中一個苯基環的所有取代基,不超過20。最佳的是,在選自R1-R5、R6-R10、R11-R15、R16-R20的取代基的任何基團中的整體C原子數不超過12。
更佳的是,此目的是藉由通式(I)的新化合物來達成,其中 i)R1-R5的至少其中之一以及R11-R15的至少其中之一是C6-C20芳基或C2-C20雜芳基,或 ii)R1與R2以及R11與R12形成芳香環,或 iii)R2與R3以及R12與R13形成芳香環 以及 R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基,而其他的R6-R10以及R16-R20是H。
甚至較佳的是,此目的是藉由通式(I)的新化合物來達成,其中 R1-R5的至少其中之一以及R11-R15的至少其中之一是C6-C20芳基或C2-C20雜芳基; R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或 R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基, 而其他的R1-R5、R6-R10、R11-R15以及R16-R20是H。
甚至更佳的是,此目的是藉由通式(I)的新化合物來達成,其中 R1-R5的至少其中之一以及R11-R15的至少其中之一是苯基; R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或 R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基, 而其他的R1-R5、R6-R10、R11-R15以及R16-R20是H。
甚至更佳的是,此目的是藉由上面定義的通式(II)或(III)的新化合物來達成,最佳的是在它們上述較佳的具體實施例中。
較佳的是,含有式(I)化合物的至少一層是電摻雜的。
更佳的是,含有式(I)化合物的層具有至少一摻雜部分以及比該摻雜部分較少摻雜或未摻雜的至少一部分。在此具體實施例中,該層的較少摻雜或未摻雜部分用以作為電子阻擋層。
在一個更較佳的具體實施例中,該層的未摻雜部分用以作為電子阻擋以及三重態激子阻擋層。
在努力尋找新方式以達成更好的OLED的研究中,本作者出乎意料地發現到,當用於包含磷光射極的OLED中時,某些長久已知的電洞傳輸材料,像是或表現得出乎意料地好,而它們在傳統螢光OLED中的性能僅為中等的,且決不可能達成由已建立的電洞傳輸基質材料所提供的程度,像是或。
進一步的研究幫助了澄清了與所測試化合物結構的關係,並確認改進是相當普遍的。表1示出了藉由下面範例中詳細描述的程序所獲得的實驗結果。在所測試的實驗OLED中,電洞傳輸層以p摻雜物摻雜,其在基板/HTL/EBL欄位中以p-符號表示。在該表中,對於顯示出比參考電壓還低的電壓的化合物,在電壓欄位中指定為負值。相反地,在電壓欄位中的正值顯示出相較於在相同條件下製備出的參考裝置組上測量到的平均電壓,在包含具創造性化合物的裝置組處觀察到了相反、較高的平均電壓。在效率欄位中,高於比較性裝置的平均效率的包含具創造性化合物的裝置的平均效率是正的,而與參考相比相反較低的效率具有負的符號。該表中最後的欄位顯示出效率欄位中的值以及電壓欄位中的值之間的算術差。所產生的值用以作為評估整體性能的基準。在三列的至少一列中的其正值顯示出,至少在一個應用中–如果該化合物用以作為EBL、作為HTL或在這兩層中–顯示出在此特定的例子中,百分比電壓改進已超過百分比效率減少,或,相反地,百分比效率改進超過了不想要的電壓增加,或在兩個特性中都有改進。在螢光藍OLED中,對於所測試的化合物一致地一點都沒有特定的(在至少一個-效率或電壓-值中)改進。因此,所有的整體性能值非常地負面。令人驚訝地,在該磷光OLED中,唯一明確失敗的測試取代基的結構特徵的組合(在所有應用中提供了負面整體性能)是被定義為具有至少一個強力拉電子基團的苯基的R23取代基。所獲得的知識用於提供新的電洞傳輸以及電子阻擋基質材料,特別有用於包含三重態射極的OLED中。
【表1】
此外,已發現到,當用以作為藍色螢光OLED中的電洞傳輸及/或電子阻擋基質時,具創造性的化合物也是有利的。
發光層、電子傳輸層、電洞阻擋層、電極
可在各種設計中並從科學與專利文獻中所描述的各種材料來製備具創造性的磷光發光裝置的除了具創造性的電洞傳輸及/或電子阻擋層之外的其他部分。
在範例中,使用了下述的支持材料:作為p摻雜物,以及E2 作為電子傳輸基質,作為n摻雜物,作為三重態射極,作為已知的電子阻擋基質。 範例3,5- 二溴苯烯的一般程序
將1,3,5-三溴苯、硼酸以及Pd(PPh3)4溶解於甲苯以及乙醇的混合物中。加入脫氣的2M Na2CO3水溶液。將該混合物回流18小時。在冷卻至室溫之後,從水相分離出有機相。將該水相以甲苯萃取三次。將所結合的有機相蒸發至乾燥,並使用二氯甲烷(DCM)作為洗提液而通過矽膠墊過濾殘餘物。蒸發溶劑之後,使用己烷:DCM混合物作為洗提液,在矽膠上藉由管柱層析純化粗產物。在薄層層析(TLC)中,上部主要的點被識別為所想要的產物,且下面的點為3,5-雙取代的溴苯副產物。
3,5- 二溴 -1,1'- 聯苯 1,3,5-三溴苯:10.20 g(1.2 eq, 32.4 mmol) 苯基硼酸:3.30 g(1.0 eq, 27.1 mmol) Pd(PPh3)4:625 mg(2 mol%, 0.54 mmol) 甲苯:160 mL 乙醇:54 mL 2M Na2CO3:27 mL 產量:5.53 g(65%) GC-MS:m/z = 310 / 312 / 314
3,5-二溴-3',5'-二甲基-1,1'-聯苯1,3,5-三溴苯:13.00 g(1.2 eq, 41.3 mmol) 3,5-二甲基苯基硼酸:5.16 g(1.0 eq, 34.4 mmol) Pd(PPh3)4:795 mg(2 mol%, 0.69 mmol) 甲苯:160 mL 乙醇:68 mL 2M Na2CO3:34 mL 產量:7.13 g(61%) GC-MS:m/z = 338 / 340 / 342
3,5-二溴-1,1':4',1''-聯三苯1,3,5-三溴苯:10.00 g(1.2 eq, 31.77 mmol) 4-聯苯硼酸:5.24 g(1.0 eq, 26.47 mmol) Pd(PPh3)4:612 mg(2 mol%, 0.53 mmol) 甲苯:160 mL 乙醇:52 mL 2M Na2CO3:26 mL 產量:4.95 g(48%) GC-MS:m/z = 386 / 388 / 390
3,5-二溴-3'-(三氟甲基)-1,1'-聯苯1,3,5-三溴苯:10.00 g(1.2 eq, 31.77 mmol) 3-(三氟甲基)苯基硼酸:5.03 g(1.0 eq, 26.47 mmol) Pd(PPh3)4:611 mg(2 mol%, 0.53 mmol) 甲苯:160 mL 乙醇:52 mL 2M Na2CO3:26 mL 產量:5.57 g(56%) GC-MS:m/z = 378 / 380 / 382
3-(3,5-二溴苯基)吡啶1,3,5-三溴苯:10.00 g(1.2 eq, 31.77 mmol) 3-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)吡啶:5.43 g(1.0 eq, 26.47 mmol) Pd(PPh3)4:612 mg(2 mol%, 0.53 mmol) 甲苯:160 mL 乙醇:52 mL 2M Na2CO3:26 mL 產量:4.00 g(48%) GC-MS:m/z = 311 / 313 / 315 以聯苯為基礎的核心的一般程序
將二溴化合物溶解於乙醚中,並以鋁箔紙保護燒瓶以避光。將溶液冷卻至-80°C,並在30分鐘內加入丁基鋰。在加入丁基鋰之後,將該溶液維持在–80°C達90分鐘。在劇烈攪拌下,一口氣加入氯化銅(II)。允許該溶液回溫至室溫,並攪拌隔夜。TLC指出起始材料的消耗以及新產物的形成,該新產物為混合物中的唯一成分。將該混合物以10%NH4OH水溶液沖洗三次,以鹽水沖洗一次,並以水沖洗一次。通過MgSO4乾燥有機相,並藉由使用DCM/己烷1:1而經由矽膠墊過濾。在蒸發溶劑之後,在煮沸的甲醇中清洗粗產物15分鐘,然後過濾並乾燥。
3,3'-二溴-1,1'-聯苯3,5-二溴苯:58.98 g(1.0 eq, 250 mmol) n-丁基鋰,2.5 M於己烷中:100 mL(1.0 eq, 250 mmol) 氯化銅(II):36,97 g(1.1 eq, 275 mmol) 二乙醚:800 mL 產量:22.06 g(56%) GC-MS:m/z = 310 / 312 / 314
3,3'-二溴-5,5'-二甲基-1,1'-聯苯3,5-二溴甲苯:62.48 g(1.0 eq, 250 mmol) n-丁基鋰,2.5 M於己烷中:100 mL(1.0 eq, 250 mmol) 氯化銅(II):36,97 g(1.1 eq, 275 mmol) 二乙醚:800 mL 產量:22.1 g(52%) GC-MS:m/z = 338 / 340 / 342
3,3'-二溴-5,5'-二甲氧基-1,1'-聯苯3,5-二溴苯甲醚:16.40 g(1.0 eq, 61.7 mmol) n-丁基鋰,2.5 M於己烷中:27 mL(1.0 eq, 67.8 mmol) 氯化銅(II):9.12 g(1.1 eq, 67.8 mmol) 二乙醚:200 mL 產量:9.7 g(85%) GC-MS:m/z = 370 / 372 / 374 二級胺的一般程序
在鈍氣下,將溴芳基成分、醋酸鈀(II)、碳酸銫以及2,2'-雙(二苯基膦)-1,1'-聯萘(BINAP)於燒瓶中結合,並溶解於1,4-二噁烷中。加入一級芳基胺成分,接著將混合物加熱至回流並攪拌18-48小時。根據TLC,反應完成。將該混合物冷卻至室溫,並經由矽膠墊過濾。在以DCM沖洗並蒸發該溶劑之後,藉由管柱層析(SiO2,己烷:DCM混合物)純化粗產物。將所結合的餾分蒸發至乾燥,並從己烷再結晶出所產生的固體,以產出想要的產物。
N-(p-甲苯基)萘-2-胺2-溴萘:15 g(1.0 eq, 72.44 mmol) p-甲苯胺:11.6 g(1.5 eq, 108.6 mmol) 醋酸鈀(II):488 mg(3.0 mol.%, 2.17 mmol) BINAP:2.0 g(4.5 mol.%, 3.26 mmol) 碳酸銫:47.20 g(2.0 eq, 144.9 mmol) 二噁烷:150 mL 產量:11.4 g(67%) GC-MS:m/z = 233
N-(4-(甲基)苯基)-[1,1'-聯苯]-4-胺4-溴聯苯:20.0 g(1.0 eq, 85.8 mmol) 4-甲苯胺:9.65 g(1.05 eq, 90.1 mmol) 醋酸鈀(II):578 mg(3.0 mol.%, 2.6 mmol) BINAP:2.40 g(4.5 mol.%, 3.9 mmol) 碳酸銫:39.14 g(1.4 eq, 120.1 mmol) 二噁烷:200 mL 產量:19.20 g(86%) EI-MS:m/z = 259
N-(4-(叔丁基)苯基)-[1,1'-聯苯]-4-胺4-溴聯苯:20 g(1.0 eq, 85.8 mmol) 4-(叔丁基)苯胺:15.36 g(1.2 eq, 102.9 mmol) 醋酸鈀(II):578 mg(3.0 mol.%, 2.57 mmol) BINAP:2.4 g(4.5 mol.%, 3.86 mmol) 碳酸銫:55.90 g(2.0 eq, 171.6 mmol) 二噁烷:220 mL 產量:13.9 g(54%) GC-MS:m/z = 301
N-(3,5-二甲基苯基)-[1,1'-聯苯]-4-胺4-溴聯苯:30.00 g(1.0 eq, 128.70 mmol) 3,5-二甲基苯胺:16.38 g(1.05 eq, 135.10 mmol) 醋酸鈀(II):867 mg(3.0 mol.%, 3.86 mmol) BINAP:3.60 g(4.5 mol.%, 5.79 mmol) 碳酸銫:58.70 g(1.4 eq, 180.00 mmol) 二噁烷:300 mL 產量:21.34 g(60%) GC-MS:m/z = 273
N-異亞丙基-[1,1'-聯苯]-4-胺4-溴聯苯:20.00 g(1.0 eq, 85.8 mmol) 異亞丙基胺:12.18 g(1.05 eq, 90.1 mmol) 醋酸鈀(II):578 mg(3.0 mol.%, 2.57 mmol) BINAP:2.40 g(4.5 mol.%, 3.86 mmol) 碳酸銫:39.13 g(1.4 eq, 120.1 mmol) 二噁烷:200 mL 產量:12.53 g(51%) GC-MS:m/z = 287 3,5-二胺基苯烯類的三級胺的一般程序
在鈍氣下,將二級胺、二溴化合物、雙(二亞苄基丙酮)鈀、三叔丁基膦以及叔丁醇鉀於燒瓶中結合,並溶解於甲苯中。將混合物在80°C攪拌80分鐘,然後冷卻至室溫。TLC指出起始材料的完全消耗。經由矽膠墊過濾該混合物,以1:2的DCM/己烷混合物沖洗,並蒸發至乾燥。在沸騰的甲醇中攪拌粗產物。在冷卻至室溫之後,過濾該混合物以產生產物。在TLC指出仍有一些雜質的情況中,使用管柱層析。最後,藉由在高度真空(10-6 mbar)的條件下的梯度昇華來純化所有的三級胺。
N1,N3-二([1,1'-聯苯]-4-基)-N1,N3-雙(4-(叔丁基)苯基)-5-甲基苯-1,3-二胺 (MPD-1)3,5-二溴甲苯:2.8 g(1.0 eq, 11.2 mmol) N-(4-(叔丁基)苯基)-[1,1'-聯苯]-4-胺:7.1 g(2.1 eq, 23.6 mmol) 雙(二亞苄基丙酮)鈀:129 mg(2 mol.%, 0.22 mmol) 三叔丁基膦:68 mg(3 mol.%, 0.34 mmol) 叔丁醇鉀:3.77 g(3.0 eq, 33.6 mmol) 甲苯:220 mL 產量:7.03 g(91%) HPLC-MS:m/z = 691 [M+H+]
5-甲基-N1,N3-二(萘-2-基)-N1,N3-二-p-甲苯基苯-1,3-二胺(MPD-2)(比較性範例)3,5-二溴甲苯:2.0 g(1.0 eq, 8.0 mmol) N-(p-甲苯基)萘-2-胺:3.92 g(2.1 eq, 16.8 mmol) 雙(二亞苄基丙酮)鈀:92 mg(2.0 mol.%, 0.16 mmol) 三叔丁基膦:49 mg(3 mol.%, 0.24 mmol) 叔丁醇鉀:2.69 g(3.0 eq, 24 mmol) 甲苯:130 mL 產量:3.95 g(70%) HPLC-MS:m/z = 555 [M+H+]
5-甲基-N1,N3-二(萘-1-基)-N1,N3-二苯基苯-1,3-二胺(MPD-3)(比較性範例)3,5-二溴甲苯:5.0 g(1.0 eq, 20.0 mmol) N-苯基萘-1-胺:9.21 g(2.1 eq, 42.0 mmol) 雙(二亞苄基丙酮)鈀:230 mg(2 mol%, 0.40 mmol) 三叔丁基膦:121 mg(3 mol.%, 0.60 mmol) 叔丁醇鉀:6.73 g(3.0 eq, 60.0 mmol) 甲苯:150 mL 產量:9.31 g(88%) HPLC-MS:m/z = 527 [M+H+]
N1,N3-二([1,1'-聯苯]-4-基)-N1,N3-雙(4-(叔丁基)苯基)-5-甲氧基苯-1,3-二胺(MPD-4)3,5-二溴苯甲醚:2.00 g(1.0 eq, 7.50 mmol) N-(4-(叔丁基)苯基)-[1,1'-聯苯]-4-胺:4.76 g(2.1 eq, 15.8 mmol) 雙(二亞苄基丙酮)鈀:86 mg(2.0 mol%, 0.15 mmol) 三叔丁基膦:46 mg(3 mol.%, 0.23 mmol) 叔丁醇鉀:2.52 g(3.0 eq, 22.5 mmol) 甲苯:130 mL 產量:5.08 g(96%) HPLC-MS:m/z = 707 [M+H+]
N3,N5-二([1,1'-聯苯]-4-基)-N3,N5-雙(3,5-二甲基苯基)-[1,1'-聯苯]-3,5-二胺(MPD-5)3,5-二溴-1,1'-聯苯:1.9 g(1.0 eq, 6.1 mmol) N-(3,5-二甲基苯基)-[1,1'-聯苯]-4-胺:3.5 g(2.1 eq, 12.8 mmol) 雙(二亞苄基丙酮)鈀:70 mg(2 mol.%, 0.12 mmol) 三叔丁基膦:37 mg(3 mol.%, 0.18 mmol) 叔丁醇鉀:2.05 g(3.0 eq, 18.3 mmol) 甲苯:150 mL 產量:2.94 g(69%) HPLC-MS:m/z = 719 [M+Na+]
N3,N5-二([1,1'-聯苯]-4-基)-N3,N5-雙(4-(叔丁基)苯基)-[1,1'-聯苯]-3,5-二胺(MPD-6)3,5-二溴-1,1'-聯苯:1.80 g(1.0 eq, 5.8 mmol) N-(4-(叔丁基)苯基)-[1,1'-聯苯]-4-胺:3.65 g(2.1 eq, 12.1 mmol) 雙(二亞苄基丙酮)鈀:66 mg(2 mol.%, 0.12 mmol) 三叔丁基膦:35 mg(3 mol.%, 0.17 mmol) 叔丁醇鉀:1.94 g(3.0 eq, 17.3 mmol) 甲苯:150 mL 產量:4.17 g(96%) HPLC-MS:m/z = 775 [M+Na+]
N1,N3-二([1,1'-聯苯]-4-基)-N1,N3-雙(3,5-二甲基苯基)-5-甲基苯-1,3-二胺(MPD-7)3,5-二溴甲苯:1.52 g(1.0 eq, 6.1 mmol) N-(3,5-二甲基苯基)-[1,1'-聯苯]-4-胺:3.50 g(2.1 eq, 12.8 mmol) 雙(二亞苄基丙酮)鈀:70 mg(2 mol.%, 0.12 mmol) 三叔丁基膦:37 mg(3 mol.%, 0.18 mmol) 叔丁醇鉀:2.05 g(3.0 eq, 18.3 mmol) 甲苯:150 mL 產量:3.42 g(78%) HPLC-MS:m/z = 657 [M+Na+]
N3,N5-二([1,1'-聯苯]-4-基)-N3,N5-雙(3,5-二甲基苯基)-3',5'-二甲基-[1,1'-聯苯]-3,5-二胺(MPD-8)3,5-二溴-3',5'-二甲基-1,1'-聯苯:2.00 g(1.0 eq, 5.88 mmol) N N-(3,5-二甲基苯基)-[1,1'-聯苯]-4-胺:3.38 g(2.1 eq, 12.4 mmol) 雙(二亞苄基丙酮)鈀:68 mg(2 mol.%, 0.12 mmol) 三叔丁基膦:36 mg(3 mol.%, 0.18 mmol) 叔丁醇鉀:1.98 g(3.0 eq, 17.6 mmol) 甲苯:120 mL 產量:4.02 g(94%) HPLC-MS:m/z = 747 [M+Na+]
N3,N5-二([1,1'-聯苯]-4-基)-N3,N5-雙(4-(叔丁基)苯基)-3',5'-二甲基-[1,1'-聯苯]-3,5-二胺(MPD-9)3,5-二溴-3',5'-二甲基-1,1'-聯苯:2.00 g(1.0 eq, 5.88 mmol) N-(4-(叔丁基)苯基)-[1,1'-聯苯]-4-胺:3.72 g(2.1 eq, 12.4 mmol) 雙(二亞苄基丙酮)鈀:68 mg(2 mol.%, 0.12 mmol) 三叔丁基膦:36 mg(3 mol.%, 0.18 mmol) 叔丁醇鉀:1.98 g(3.0 eq, 17.6 mmol) 甲苯:120 mL 產量:4.43 g(97%) HPLC-MS:m/z = 803 [M+Na+]
N1,N3-二([1,1'-聯苯]-4-基)-N1,N3-雙(4-(叔丁基)苯基)-5-(吡啶-3-基)苯-1,3-二胺(MPD-10)3-(3,5-二溴苯基)吡啶:1.50 g(1.0 eq, 4.8 mmol) N-(4-(叔丁基)苯基)-[1,1'-聯苯]-4-胺:3.0 g(2.1 eq, 10.1 mmol) 雙(二亞苄基丙酮)鈀:55 mg(2 mol.%, 0.10 mmol) 三叔丁基膦:29 mg(3 mol.%, 0.14 mmol) 叔丁醇鉀:1.62 g(3.0 eq, 14.4 mmol) 甲苯:120 mL 產量:2.40 g(66%) HPLC-MS:m/z = 754 [M+H+]
N3,N5-二([1,1'-聯苯]-4-基)-N3,N5-雙(4-(叔丁基)苯基)-3'-(三氟甲基)-[1,1'-聯苯]-3,5-二胺(MPD-11)3,5-二溴-3'-(三氟甲基)-1,1'-聯苯:1.82 g(1.0 eq, 4.8 mmol) N-(4-(叔丁基)苯基)-[1,1'-聯苯]-4-胺:3.0 g(2.1 eq, 10.1 mmol) 雙(二亞苄基丙酮)鈀:55 mg(2 mol.%, 0.10 mmol) 三叔丁基膦:29 mg(3 mol.%, 0.14 mmol) 叔丁醇鉀:1.62 g(3.0 eq, 14.4 mmol) 甲苯:120 mL 產量:3.29 g(84%) HPLC-MS:m/z = 843 [M+Na+]
N3,N5-二([1,1'-聯苯]-4-基)-N3,N5-雙(4-(叔丁基)苯基)-[1,1':4',1''-聯三苯]-3,5-二胺(MPD-12)3,5-二溴-1,1':4',1''-聯三苯:1.86 g(1.0 eq, 4.8 mmol) N-(4-(叔丁基)苯基)-[1,1'-聯苯]-4-胺:3.03 g(2.1 eq, 10.1 mmol) 雙(二亞苄基丙酮)鈀:55 mg(2 mol.%, 0.10 mmol) 三叔丁基膦:29 mg(3 mol.%, 0.14 mmol) 叔丁醇鉀:1.62 g(3.0 eq, 14.4 mmol) 甲苯:120 mL 產量:3.20 g(80%) HPLC-MS:m/z = 851 [M+Na+]
N1,N3-二([1,1'-聯苯]-4-基)-N1,N3-雙(4-(叔丁基)苯基)苯-1,3-二胺(MPD-13)3,5-二溴苯:2.5 g(1.0 eq, 10.6 mmol) N-(4-(叔丁基)苯基)-[1,1'-聯苯]-4-胺:6.70 g(2.1 eq, 22.26 mmol) 雙(二亞苄基丙酮)鈀:121 mg(2 mol.%, 0.21 mmol) 三叔丁基膦:64 mg(3 mol.%, 0.32 mmol) 叔丁醇鉀:3.57 g(3.0 eq, 31.8 mmol) 甲苯:180 mL 產量:6.70 g(94%) ESI-MS:m/z = 677 [M+H+]
N1,N3-二([1,1'-聯苯]-4-基)-N1,N3-雙(3,5-二甲基苯基)苯-1,3-二胺(MPD-14)3,5-二溴苯:2.5 g(1.0 eq, 10.6 mmol) N-(3,5-二甲基苯基)-[1,1'-聯苯]-4-胺:6.08 g(2.1 eq, 22.26 mmol) 雙(二亞苄基丙酮)鈀:122 mg(2 mol.%, 0.21 mmol) 三叔丁基膦:64 mg(3 mol.%, 0.32 mmol) 叔丁醇鉀:3.57 g(3.0 eq, 31.8 mmol) 甲苯:180 mL 產量:5.42 g(82%) ESI-MS:m/z = 621 [M+H+]
N1,N3-二([1,1'-聯苯]-4-基)-5-甲基-N1,N3-二-p-甲苯基苯-1,3-二胺(MPD-15)3,5-二溴甲苯:2.5 g(1.0 eq, 10.0 mmol) N-(4-(甲基)苯基)-[1,1'-聯苯]-4-胺:5.45 g(2.1 eq, 21.00 mmol) 雙(二亞苄基丙酮)鈀:115 mg(2 mol.%, 0.20 mmol) 三叔丁基膦:61 mg(3 mol.%, 0.30 mmol) 叔丁醇鉀:3.37 g(3.0 eq, 30.0 mmol) 甲苯:180 mL 產量:4.95 g(81%). ESI-MS:m/z = 607 [M+H+]
N1,N3-二([1,1'-聯苯]-4-基)-N1,N3-二異亞丙基-5-甲基苯-1,3-二胺(MPD-16)3,5-二溴甲苯:16.60 g(1.0 eq, 66.4 mmol) N-異亞丙基-[1,1'-聯苯]-4-胺:40.1 g(2.1 eq, 139.5 mmol) 雙(二亞苄基丙酮)鈀:764 mg(2 mol.%, 1.3 mmol) 三叔丁基膦:404 mg(3 mol.%, 2.00 mmol) 叔丁醇鉀:22.36 g(3.0 eq, 199.3 mmol) 甲苯:400 mL 產量:22.3 g(51%) HPLC-MS:m/z = 663 [M+H+] 3,3’-二胺基聯苯烯類的三級胺的一般程序
將二溴化合物、二級胺、雙(二亞苄基丙酮)鈀、三叔丁基膦以及叔丁醇鉀在燒瓶中結合,並溶解於甲苯中。將混合物於80°C攪拌,直到TLC指出起始材料的完全消耗。經由矽膠墊過濾該混合物,以DCM沖洗並蒸發至乾燥。在沸騰的甲醇中清洗粗固體,之後將其過濾。以熱己烷以及熱丙酮重複此順序,以最終產出想要的產物。
N3,N3'-二([1,1'-聯苯]-4-基)-N3,N3'-雙(4-(叔丁基)苯基)-5,5'-二甲基-[1,1'-聯苯]-3,3'-二胺(MDAB-1)3,3'-二溴-5,5'-二甲基-1,1'-聯苯:2.00 g(1.0 eq, 5.88 mmol) N-(4-(叔丁基)苯基)-[1,1'-聯苯]-4-胺:3.90 g(2.1 eq, 12.9 mmol) 雙(二亞苄基丙酮)鈀:68 mg(2.0 mol.%, 0.12 mmol) 三叔丁基膦:36 mg(3.0 mol.%, 0.18 mmol) 叔丁醇鉀:1.98 g(3.0 eq, 17.6 mmol) 甲苯:150 mL 產量:2.27 g(49%) HPLC-MS:m/z = 781 [M+H+]
N3,N3'-二([1,1'-聯苯]-4-基)-N3,N3'-雙(4-(叔丁基)苯基)-5,5'-二甲氧基-[1,1'-聯苯]-3,3'-二胺(MDAB-2)3,3'-二溴-5,5'-二甲氧基-1,1'-聯苯:2.00 g(1.0 eq, 5.88 mmol) N-(4-(叔丁基)苯基)-[1,1'-聯苯]-4-胺:3.56 g(2.2 eq, 11.8 mmol) 雙(二亞苄基丙酮)鈀:62 mg(2.0 mol.%, 0.11 mmol) 三叔丁基膦:33 mg(3.0 mol.%, 0.16 mmol) 叔丁醇鉀:1.81 g(3.0 eq, 16.1 mmol) 甲苯:130 mL 產量:3.33 g(76%) HPLC-MS:m/z = 835 [M+Na+]
N3,N3'-二([1,1'-聯苯]-4-基)-N3,N3'-雙(3,5-二甲基苯基)-5,5'-二甲基-[1,1'-聯苯]-3,3'-二胺(MDAB-3)3,3'-二溴-5,5'-二甲基-1,1'-聯苯:5.43 g(1.0 eq, 15.96 mmol) N-(3,5-二甲基苯基)-[1,1'-聯苯]-4-胺:9.61 g(2.1 eq, 33.51 mmol) 雙(二亞苄基丙酮)鈀:184 mg(2.0 mol.%, 0.32 mmol) 三叔丁基膦:202 mg(3.0 mol.%, 0.48 mmol) 叔丁醇鉀:5.37 g(3.0 eq, 47.88 mmol) 甲苯:250 mL 產量:10.56 g(91%) HPLC-MS:m/z = 747 [M+Na+]
N3,N3'-二([1,1'-聯苯]-4-基)-N3,N3'-二苯基-[1,1'-聯苯]-3,3'-二胺(MDAB-4)3,3'-二溴-1,1'-聯苯:3.39 g(1.0 eq, 10.88 mmol) N-(3,5-二甲基苯基)-[1,1'-聯苯]-4-胺:5.60 g(2.1 eq, 22.84 mmol) 雙(二亞苄基丙酮)鈀:125 mg(2.0 mol.%, 0.22 mmol) 三叔丁基膦:66 mg(3.0 mol.%, 0.33 mmol) 叔丁醇鉀:3.66 g(3.0 eq, 32.6 mmol) 甲苯:190 mL 產量:6.8 g(97%) EI-MS:m/z = 640
5,5'-二甲基-N3,N3,N3',N3'-四-m-甲苯基-[1,1'-聯苯]-3,3'-二胺(MDAB-5)3,3'-二溴-5,5'-二甲基-1,1'-聯苯:2.50g(1.0 eq, 7.35mmol) 3,3’-二甲基二苯基胺:3.05 g(2.1 eq, 15.44 mmol) 雙(二亞苄基丙酮)鈀:85 mg(2.0 mol.%, 0.15 mmol) 三叔丁基膦:45 mg(3.0 mol.%, 0.22 mmol) 叔丁醇鉀:2.50 g(3.0 eq, 22.05 mmol) 甲苯:180 mL 產量:2.8 g(66%) EI-MS:m/z = 572
N3,N3'-二([1,1'-聯苯]-4-基)-N3,N3'-二異亞丙基-5,5'-二甲基-[1,1'-聯苯]-3,3'-二胺(MDAB-6)3,5-二溴-3',5'-二甲基-1,1'-聯苯:20.00 g(1.0 eq, 58.8 mmol) N-異亞丙基-[1,1'-聯苯]-4-胺:35.50 g(2.1 eq, 123.5 mmol) 雙(二亞苄基丙酮)鈀:676 mg(2 mol.%, 1.20 mmol) 三叔丁基膦:364 mg(3 mol.%, 1.80 mmol) 叔丁醇鉀:19.80 g(3.0 eq, 176.4 mmol) 甲苯:700 mL 產量:27.1 g(61%) HPLC-MS:m/z = 753 [M+H+]
N3,N3'-二([1,1'-聯苯]-4-基)-N3,N3'-二異亞丙基-[1,1'-聯苯]-3,3'-二胺(MDAB-7)3,5-二溴-1,1'-聯苯:5.17 g(1.0 eq, 16.59 mmol) N-異亞丙基-[1,1'-聯苯]-4-胺:10.00 g(2.1 eq, 34.79 mmol) 雙(二亞苄基丙酮)鈀:190 mg(2 mol.%, 0.33 mmol) 三叔丁基膦:100 mg(3 mol.%, 0.50 mmol) 叔丁醇鉀:5.58 g(3.0 eq, 49.77 mmol) 甲苯:230 mL 產量:8.7 g(72%) EI-MS:m/z = 724 OLED製備以及測試
在底部發光磷光有機發光二極管(OLED)中進行新材料的性能測試。在真空中經由熱氣相沉積有機材料(主動層)以及金屬(電極)處理該二極管。使用蔽蔭遮罩技術來建構該裝置(主動矩陣、電極)。在一個基板上製備四個OLED,每個具有6.70 mm2的主動區域。16個相同的氧化銦錫(ITO)基板以4x4的陣列放在可繞著其垂直軸樞軸轉動的桌上並被立即處理。使用遮光器,這16個基板每個可由不同組的有機層覆蓋。清洗該ITO基板,並將其以4x4的陣列放到熱氣相沉積單元中。將參考p摻雜層(例如以D1摻雜的H-1;莫耳比(97:3))沉積在這些基板的一半上達30 nm的最終薄膜厚度。在板子的另一半上,以相同的97:3莫耳比以及厚度來共同沉積所研究具創造性的材料與相同的p摻雜物。在旋轉該板子90°之後,在第一層的頂部上沉積了第二(電子阻擋)層。這裡,該板子的一半是以10 nm的該參考化合物(例如,TCTA)覆蓋,且另一半以與該第一層(見第1圖)中所使用相同的具創造性的材料來覆蓋。因此該參考裝置(第1圖,區域D)總是與包含該具創造性材料的裝置一起處理。此方法允許獨立於可能的每天沉積率變異、真空品質或其他的工具性能參數,而與該參考值來相比而評估新材料的性能。由於每個區域含有16個同一製備的OLED,並對於這16個OLED的每一個估計了性能參數,所獲得實驗結果的統計學評估明確地顯示出表1中所報導觀察到的平均值的統計學顯著性。隨後的綠磷光發光層(Merck_TMM004:Irrpy以莫耳比9:1)以20 nm的厚度沉積,接著以10 nm Merck_TMM004(作為電洞阻擋層)以及摻雜有D2的50 nm E-1層(基質比摻雜物莫耳比9:1)。藉由真空沉積100 nm鋁層來製備陰極。
在ITO基板上製備底部發光藍色螢光OLED,並以類似的方式測試,不同的是,Sun Fine Chem(SFC,韓國)主持的ABH113與藍色射極NUBD370以重量比97:3共同沉積為20 nm厚的發光層,接著是由60重量%的E2以及40重量%的8-羥基喹啉鋰鹽(LiQ)構成的36 nm厚的電子傳輸層。該100 nm的鋁陰極被沉積在該電子傳輸層的頂部上。
相較於在相同的電洞傳輸及/或電子阻擋層中包含H-2的裝置,包含具創造性的化合物的裝置顯示出關於如表1中所定義整體性能分數Q在範圍3-22%中的改進。
前述描述中以及申請專利範圍中所揭露的特徵可,分開地或以任何組合,為用於實現其不同形式的本發明的材料。
1...基板
2...基極
3...電洞注入層
4...電洞傳輸層(HTL)
5...發光層(EL)
6...電子傳輸層(ETL)
7...電子注入層
8...加罩電極
9...封裝
A、B、C、D...區域
第1圖:實驗性底部發光磷光OLED的示意圖 第2圖:a)層1(p-摻雜的具創造性材料(條紋)、p摻雜參考(點),左側)沉積的俯視圖;b)在旋轉基板90°之後層2的俯視圖,該具創造性的材料在上排(區域A、C)以及參考材料在下排(區域B、D)。 第3a圖至第 3g圖:在CD2Cl2溶液中,以500.13 MHz、參考至5.31 ppm所測量具有式(II)的範例化合物的1H-NMR光譜;3a – MDAB-1, 3b – MDAB-2, 3c – MDAB-3, 3d – MDAB-4, 3e – MDAB-5, 3f – MDAB-6, 3g – MDAB-7。 第4a 圖至第 4o圖:在相同條件下測量具有式(III)的範例化合物的1H-NMR光譜;4a – MPD-1, 4b – MPD-2, 4c – MPD-3, 4d – MPD-4, 4e – MPD-5, 4f – MPD-6, 4g – MPD-7, 4h – MPD-8, 4i – MPD-9, 4j – MPD-10, 4k – MPD-11, 4l – MPD-12, 4m – MPD-13, 4n – MPD-14, 4o – MPD-15。
無。
Claims (14)
- 一種在陽極以及陰極之間包含至少一發光層的有機發光裝置,該至少一發光層包含一磷光射極以及至少一電洞傳輸及/或電子阻擋層,該至少一電洞傳輸及/或電子阻擋層包含由通式(I)表示的一化合物其中R1-R20可獨立地選自氫、C1-C20烷基或C3-C20環烷基、C1-C20烷氧基或C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基, i)R1-R5的至少其中之一以及R11-R15的至少其中之一是C6-C20芳基或C2-C20雜芳基,或 ii)R1與R2以及R11與R12形成一芳香環,或 iii)R2與R3以及R12與R13形成一芳香環; R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基 以及 x是選自0以及1的一整數,其中對於x=0,R22具有與R1-R20相同的意義,而對於x=1,R21以及R22獨立地選自氫、C1-C10烷基、C3-C10環烷基、C1-C10烷氧基以及C3-C10環烷基氧基。
- 如申請專利範圍第1項所述的裝置,其中R1-R5的至少其中之一以及R11-R15的至少其中之一是C6-C20芳基或C2-C20雜芳基,而其他的R1-R5以及R11-R15是氫。
- 如申請專利範圍第1項至第2項中任一項所述的裝置,其中R1-R5的至少其中之一以及R11-R15的至少其中之一是苯基,而其他的R1-R5以及R11-R15是氫。
- 如申請專利範圍第1項至第3項中任一項所述的裝置,其中R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基。
- 如申請專利範圍第1項至第4項中任一項所述的裝置,其中x=1,以及R21與R22是獨立地選自甲基或甲氧基。
- 如申請專利範圍第1項至第4項中任一項所述的裝置,其中x=1,以及R21與R22是相同的。
- 如申請專利範圍第1項至第6項中任一項所述的裝置,其中含有式(I)的該化合物的至少一層是電摻雜的。
- 如申請專利範圍第7項所述的裝置,其中含有式(I)的該化合物的該層具有至少一摻雜部分以及比該摻雜部分還少摻雜的或未摻雜的至少一部分。
- 一種由通式(I)表示的化合物其中R1-R20可獨立地選自氫、C1-C20烷基或C3-C20環烷基、C1-C20烷氧基或C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基, i)R1-R5的至少其中之一以及R11-R15的至少其中之一是C6-C20芳基或C2-C20雜芳基,或 ii)R1與R2以及R11與R12形成一芳香環,或 iii)R2與R3以及R12與R13形成一芳香環; R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基 以及 x是選自0以及1的一整數,其中對於x=0,R22具有與R1-R20相同的意義,而對於x=1,R21以及R22獨立地選自氫、C1-C10烷基、C3-C10環烷基、C1-C10烷氧基以及C3-C10環烷基氧基。
- 如申請專利範圍第9項所述的化合物,其中 i)R1-R5的至少其中之一以及R11-R15的至少其中之一是C6-C20芳基或C2-C20雜芳基或 ii)R1與R2以及R11與R12形成一芳香環,或 iii)R2與R3以及R12與R13形成一芳香環; R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基,而其他的R6-R10以及R16-R20是H。
- 如申請專利範圍第10項所述的化合物,其中 R1-R5的至少其中之一以及R11-R15的至少其中之一是C6-C20芳基或C2-C20雜芳基; R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或 R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基, 而其他的R1-R5、R6-R10、R11-R15以及R16-R20是H,以及 x是選自0以及1的一整數,其中對於x=0,R22具有與R1-R20相同的意義,而對於x=1,R21以及R22是獨立地選自C1-C10烷基、C3-C10環烷基、C1-C10烷氧基以及C3-C10環烷基氧基。
- 如申請專利範圍第11項所述的化合物,其中 R1-R5的至少其中之一以及R11-R15的至少其中之一是苯基; R6-R10的至少其中兩個以及R16-R20的至少其中兩個是甲基,或 R6-R10的至少其中之一以及R16-R20的至少其中之一是選自C2-C20烷基、C3-C20環烷基、C1-C20烷氧基、C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基, 而其他的R1-R5、R6-R10、R11-R15以及R16-R20是H。
- 如申請專利範圍第12項所述的化合物,由式(II)表示其中R23是氫、C1-C20烷基或C3-C20環烷基、C1-C10烷氧基或C3-C20環烷基氧基、C7-C20芳基烷基、C6-C20芳基以及C2-C20雜芳基,以及Ar是選自4-叔丁基苯基、3,5-二甲基苯基以及2,4,6-三甲基苯基。
- 如申請專利範圍第1項所述的化合物,由式(III)表示其中Ar1是選自4-叔丁基苯基、3,5-二甲基苯基以及2,4,6-三甲基苯基,以及R24是選自C1-C10烷基、C3-C10環烷基、C1-C10烷氧基以及C3-C10環烷基氧基。
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2012
- 2012-10-17 EP EP12188828.3A patent/EP2722908A1/en not_active Withdrawn
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2013
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- 2013-10-17 KR KR1020157012196A patent/KR102163089B1/ko active IP Right Grant
- 2013-10-17 CN CN201380054463.XA patent/CN104838517B/zh active Active
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- 2013-10-17 EP EP13777089.7A patent/EP2909872B1/en active Active
- 2013-10-17 JP JP2015537255A patent/JP6329954B2/ja active Active
- 2013-10-17 TW TW102137587A patent/TW201422568A/zh unknown
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2019
- 2019-03-01 US US16/290,164 patent/US10868254B2/en active Active
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EP2909872B1 (en) | 2020-01-08 |
US10868254B2 (en) | 2020-12-15 |
CN104838517A (zh) | 2015-08-12 |
KR102163089B1 (ko) | 2020-10-07 |
US20190198767A1 (en) | 2019-06-27 |
JP6329954B2 (ja) | 2018-05-23 |
EP2909872A1 (en) | 2015-08-26 |
CN104838517B (zh) | 2017-10-24 |
EP2722908A1 (en) | 2014-04-23 |
KR20150066585A (ko) | 2015-06-16 |
WO2014060526A1 (en) | 2014-04-24 |
US10243146B2 (en) | 2019-03-26 |
JP2016502749A (ja) | 2016-01-28 |
US20150287930A1 (en) | 2015-10-08 |
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