TWI705062B - 電子裝置用的材料 - Google Patents
電子裝置用的材料 Download PDFInfo
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- TWI705062B TWI705062B TW105102516A TW105102516A TWI705062B TW I705062 B TWI705062 B TW I705062B TW 105102516 A TW105102516 A TW 105102516A TW 105102516 A TW105102516 A TW 105102516A TW I705062 B TWI705062 B TW I705062B
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- 239000000463 material Substances 0.000 title description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 171
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical group C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims description 107
- -1 indenocarbazolyl group Chemical group 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 230000000903 blocking effect Effects 0.000 claims description 13
- 239000000412 dendrimer Substances 0.000 claims description 13
- 229920000736 dendritic polymer Polymers 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 238000005401 electroluminescence Methods 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 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 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 230000002950 deficient Effects 0.000 claims description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 108091008695 photoreceptors Proteins 0.000 claims description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 235000021286 stilbenes Nutrition 0.000 claims description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 89
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 21
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- 239000011159 matrix material Substances 0.000 description 18
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 16
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229910052709 silver Inorganic materials 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 0 CC1(*)c(cc(cc2)-c3ccccc3)c2-c2c1cc(C)cc2 Chemical compound CC1(*)c(cc(cc2)-c3ccccc3)c2-c2c1cc(C)cc2 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 150000004982 aromatic amines Chemical group 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 125000005266 diarylamine group Chemical group 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 150000003254 radicals Chemical group 0.000 description 6
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000004327 boric acid Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 125000005259 triarylamine group Chemical group 0.000 description 5
- 229910052727 yttrium Inorganic materials 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-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
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 3
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920000144 PEDOT:PSS Polymers 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000005577 anthracene group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000010129 solution processing Methods 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005092 sublimation method Methods 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 2
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-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
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 2
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical compound C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- IQSNQFWOTIWELP-UHFFFAOYSA-N O1C(=CC=C2C1=CC=1C=CC=CC12)C(=O)N Chemical compound O1C(=CC=C2C1=CC=1C=CC=CC12)C(=O)N IQSNQFWOTIWELP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
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- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 description 1
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- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
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- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
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- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 238000007832 transition metal-catalyzed coupling reaction Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 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 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C07—ORGANIC CHEMISTRY
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
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Abstract
本申請案關於一種化合物,其含有茚并咔唑基、特定芳胺基和鍵結至該茚并咔唑基之缺電子基。該化合物係適合使用於電子裝置中,特別是於有機電致發光裝置中。
Description
本申請案關於用於電子裝置(特別是用於有機電致發光裝置)中之材料,及關於包含此等材料之電子裝置。
電子裝置就本申請案之意義而言特別意指所謂的包含有機半導體材料作為功能材料之有機電子裝置。同樣特別地,此等裝置意指在下述本發明的詳細說明中所指示之有機電致發光裝置(OLED)及其他電子裝置。
一般而言,術語OLED意指包含至少一種有機材料且在施加電壓後發光之電子裝置。OLED之確切結構尤其闡述於US 4539507、US 5151629、EP 0676461及WO 98/27136中。
主要興趣為改良電子裝置(特別是OLED)之性能數據,特別是壽命和效率以及操作電壓。有機發光體層(特別是有基質材料存在於其中)及具有電子傳輸功能之有機層在此發揮重要作用。
為了達成此技術目標,持續研究適合用作為發光層
(特別是磷光發光層)中之基質材料的新穎材料。此外,尋求具有電子傳輸及/或電洞阻擋性質之材料以用於對應功能層中。
磷光發光層就本申請案之意義而言為包含至少一種磷光發光體化合物之有機層。
發光層之發光體化合物通常為在操作電子裝置時發光之化合物。
根據本申請案之術語磷光發光體涵蓋經由自旋禁止躍遷(例如自激發三重態或具有相對較高自旋量子數的狀態(例如五重態)之躍遷)進行發光之化合物。
包含二或多種材料之系統中的基質材料意指其在混合物中之比例較大的成分。對應地,包含二或多種材料之系統中的摻雜劑意指其在混合物中之比例較小的成分。在許多情形下亦使用術語主體材料來代替術語基質材料。
若將發光體化合物與一或多種其他化合物組合使用於發光層中,則其在混合物中之比例通常相對較小。在此情形下,其亦可稱為摻雜劑化合物。一或多種其他化合物通常以相對較大比例存在於混合物中且根據上述定義可因此稱為基質材料。
自先前技術(例如自WO 2010/136109及WO 2011/000455)已知含有一或多種茚并咔唑基團之化合物於電子裝置的用途。
此外自先前技術(例如自WO 2010/015306、WO 2007/063754及WO 2008/056746)已知含有一或多種缺電
子雜芳族六員環之化合物於電子裝置的用途。
先前技術此外再次揭示含有至少一種缺電子雜芳族六員環、至少一種芳胺基和至少一種茚并咔唑基之化合物於電子裝置的用途。該等化合物及彼等在電子裝置之用途係揭示例如在WO 2010/136109和WO 2014/090368中。
然而,仍然需要改良有機電致發光裝置。更具體地說,在螢光以及磷光OLED的情況下,也應改良效率。就OLED操作壽命而言亦需要改良,特別是在藍色發光的情況下。此外,在螢光和磷光OLED二種的情況下,為了改良功率效率,非常需要減少操作電壓。這是非常重要的,特別是對於移動應用。
考慮磷光發光體之基質材料,需要改良,以使此等材料導致使用彼等的有機電致發光裝置之良好效率、長壽命和低操作電壓。特別地,基質材料的性質常常限制了電致發光裝置之壽命和效率。
令人驚訝地,現已發現:使用某些經由其N原子連結至缺電子六員雜芳族環且包含特定芳胺基之茚并咔唑化合物可達成極佳性能數據。特別地,在用於有機電致發光裝置中時,達成極佳壽命及功率效率。
本申請因此關於一種式(1)之化合物,
其中Y 相同或不同地等於N或CR1,其中六員環中至少一個基團Y必須等於N;W 相同或不同地等於CR1或N;V 相同或不同地等於CR1或N,其先決條件為二個相鄰的基團V=V表示式(2)之基團
其中虛線鍵表示此單元的連接;X 為選自下列之二價橋:N(R2)、B(R2)、O、C(R2)2、Si(R2)2、C=NR2、C=C(R2)2、S、S=O、SO2、P(R2)和P(=O)R2;Ar1、Ar2相同或不同地為芳族或雜芳環系統,其可經一或多個基團R1取代;其中基團Ar1或Ar2中至少一者表示具有12至30個芳族C原子之芳族環系統、具有13至30個芳族環原子之雜芳基或具有10至20個芳族C原子之芳基,彼等各自可經一或多個基團R1取代,Ar1和Ar2也可以基團E彼此連接;Ar3、Ar4在每次出現時相同或不同地為具有6至40個芳族C原子之芳族環系統或具有5至40個芳族環原子之雜芳族環系統,其可經一或多個基團R1取代;其先決條件為Ar4不為伸蒽基;E 為單鍵、N(R3)、O、S、C(R3)2、C(R3)2-C(R3)2、Si(R3)2或B(R3)2;R1 在每次出現時相同或不同地為H、D、F、Br、Cl、I、C(=O)R3、CN、Si(R3)3、N(R3)2、P(=O)(R3)2、S(=O)R3、S(=O)2R3、具有1至20個C原子之直鏈烷
基或烷氧基或具有3至20個C原子之支鏈或環狀烷基或烷氧基或具有2至20個C原子之烯基或炔基(其中上述基團各自可經一或多個基團R3取代且其中上述基團中之一或多個CH2基團可經-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SO或SO2置換)、或具有5至30個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R3取代)、或具有5至30個芳族環原子之芳氧基或雜芳氧基(其可經一或多個基團R3取代),其中位於Ar1上之二個相鄰的基團R1或位於Ar2上之二個相鄰的基團R1可彼此連接且可形成環;R2 在每次出現時相同或不同地為H、D、F、Br、Cl、I、C(=O)R3、CN、Si(R3)3、N(R3)2、P(=O)(R3)2、S(=O)R3、S(=O)2R3、具有1至20個C原子之直鏈烷基或烷氧基或具有3至20個C原子之支鏈或環狀烷基或烷氧基或具有2至20個C原子之烯基或炔基(其中上述基團各自可經一或多個基團R3取代且其中上述基團中之一或多個CH2基團可經-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SO或SO2置換)、或具有5至30個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R3取代)、或具有5至30個芳族環原子之芳氧基或雜芳氧基(其可
經一或多個基團R3取代);其中二個基團R2可彼此連接且可形成環;R3 在每次出現時相同或不同地為H、D、F、Br、Cl、I、C(=O)R4、CN、Si(R4)3、N(R4)2、P(=O)(R4)2、S(=O)R4、S(=O)2R4、具有1至20個C原子之直鏈烷基或烷氧基或具有3至20個C原子之支鏈或環狀烷基或烷氧基或具有2至20個C原子之烯基或炔基(其中上述基團可各自經一或多個基團R4取代且其中上述基團中之一或多個CH2基團可經-R4C=CR4-、-C≡C-、Si(R4)2、C=O、C=NR4、-C(=O)O-、-C(=O)NR4-、NR4、P(=O)(R4)、-O-、-S-、SO或SO2置換)、或具有5至30個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R4取代)、或具有5至30個芳族環原子之芳氧基或雜芳氧基(其可經一或多個基團R4取代),其中二或更多個基團R3可彼此連接且可形成環;R4 在每次出現時相同或不同地為H、D、F或具有1至20個C原子的脂族、芳族和雜芳族有機基團,此外,其中一個或多個H原子可經D或F置換;二或多個取代基R4在此可彼此連接且可形成環;n 等於0或1;m 等於0或1。
就本申請案之目的而言,下列化學基團之定義適用:芳基就本發明之意義而言含有6至60個芳族環原
子;雜芳基就本發明之意義而言含有5至60個芳族環原子,其中至少一者為雜原子。雜原子較佳地選自N、O及S。此表示基本定義。如果在本發明說明中指示其它較佳選擇,例如有關所存在之芳族環原子或雜原子的數目,則這些適用。
芳基或雜芳基在此意指簡單芳族環,即苯,或簡單雜芳族環,例如吡啶、嘧啶或噻吩,或縮合(稠合(annellated))芳族或雜芳族多環,例如萘、菲、喹啉或咔唑。縮合(稠合)芳族或雜芳族多環就本申請案的意義而言由二或多個簡單芳族或雜芳族環彼此縮合而組成。
在各情況下可被上述基團取代且可經由任何所要位置連結至芳族或雜芳族環系統之芳基或雜芳基特別意指衍生自下列之基團:苯、萘、蒽、菲、芘、二氫芘、(chrysene)、苝、丙二烯合茀(fluoranthene)、苯并蒽、苯并菲、稠四苯、稠五苯、苯并芘、呋喃、苯并呋喃、異苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、異苯并噻吩、二苯并噻吩、吡咯、吲哚、異吲哚、咔唑、吡啶、喹啉、異喹啉、吖啶、啡啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、啡噻、啡、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑(phenanthrimidazole)、吡啶并咪唑、吡咪唑、喹啉并咪唑、唑、苯并唑、萘并唑、蒽并唑、菲并唑、異唑、1,2-噻唑、1,3-噻唑、苯并噻唑、嗒、苯并嗒、嘧啶、苯并嘧啶、喹啉、吡、啡、啶、氮雜咔唑、苯并咔啉、啡啉、
1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三、1,2,4-三、1,2,3-三、四唑、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四、嘌呤、蝶啶、吲及苯并噻二唑。
芳氧基根據本發明之定義意指經由氧原子鍵結之如上所定義的芳基。類似定義適用於雜芳氧基。
芳族環系統就本發明之意義而言在環系統中含有6至60個C原子。雜芳族環系統就本發明之意義而言含有5至60個芳族環原子,其中至少一個為雜原子。雜原子較佳地選自N、O及/或S。芳族或雜芳族環系統就本發明之意義而言意指不一定只含有芳基或雜芳基,而是其中另外多個芳基或雜芳基可以非芳族單元(較佳為少於10%非H之原子)(諸如,例如sp3-混成之C、Si、N或O原子、sp2-混成之C或N原子或sp-混成之C原子)連接的系統。因此,例如系統諸如9,9’-螺雙茀、9,9’-二芳基茀、三芳基胺、二芳基醚、二苯乙烯、等等就本發明之意義而言亦意欲為芳族環系統,如為其中二或多個芳基例如以直鏈或環狀烷基、烯基或炔基或以矽基連接之系統。此外,其中二或多個芳基或雜芳基係經由單鍵彼此連結之系統就本發明之意義而言亦為芳族或雜芳族環系統,諸如,例如聯苯、聯三苯或二苯基三之系統。
在各情況下亦可經如上述定義之基團取代且可經由任何所要位置連接至芳族或雜芳族基團之具有5-60個芳族
環原子的芳族或雜芳族環系統特別意指衍生自下列之基團:苯、萘、蒽、苯并蒽、菲、苯并菲、芘、(chrysene)、苝、丙二烯合茀(fluoranthene)、稠四苯、稠五苯、苯并芘、聯苯、伸聯苯(biphenylene)、聯三苯(terphenyl)、伸聯三苯(terphenylene)、聯四苯、茀、螺二茀、二氫菲、二氫芘、四氫芘、順-或反-茚并茀、三聚茚(truxene)、異三聚茚(isotruxene)、螺三聚茚、螺異三聚茚、呋喃、苯并呋喃、異苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、異苯并噻吩、二苯并噻吩、吡咯、吲哚、異吲哚、咔唑、吲哚并咔唑、茚并咔唑、吡啶、喹啉、異喹啉、吖啶、啡啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、啡噻、啡、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑(naphthimidazole)、菲并咪唑(phenanthrimidazole)、吡啶并咪唑(pyridimidazole)、吡并咪唑(pyrazinimidazole)、喹啉并咪唑(quinoxalinimidazole)、唑、苯并唑、萘并唑(naphthoxazole)、蒽并唑(anthroxazole)、菲并唑(phenanthroxazole)、異唑、1,2-噻唑、1,3-噻唑、苯并噻唑、嗒、苯并嗒、嘧啶、苯并嘧啶、喹啉、1,5-二氮雜蒽、2,7-二氮雜芘、2,3-二氮雜芘、1,6-二氮雜芘、1,8-二氮雜芘、4,5-二氮雜芘、4,5,9,10-四氮雜苝、吡、啡、啡、啡噻熒紅環(fluorubin)、啶、氮雜咔唑、苯并咔啉、啡啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二
唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三、1,2,4-三、1,2,3-三、四唑、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四、嘌呤、喋啶、吲和苯并噻二唑或此等基團之組合。
就本發明的目的而言,具有1至40個C原子之直鏈烷基或具有3至40個C原子之支鏈或環狀烷基或具有2至40個C原子之烯基或炔基,其中,此外,個別H原子或CH2基團可經在上述該等基團定義下之基團取代,較佳意指甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、2-甲基丁基、正戊基、第二戊基、環戊基、新戊基、正己基、環己基、新己基、正庚基、環庚基、正辛基、環辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、環戊烯基、己烯基、環己烯基、庚烯基、環庚烯基、辛烯基、環辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基。具有1至40個C原子之烷氧基或烷硫基(thioalkyl)較佳意指甲氧基、三氟甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第二丁氧基、第三丁氧基、正戊氧基、第二戊氧基、2-甲基丁氧基、正己氧基、環己氧基、正庚氧基、環庚氧基、正辛氧基、環辛氧基、2-乙基己氧基、五氟乙氧基、2,2,2-三氟乙氧基、甲硫基、乙硫基、正丙硫基、異丙硫基、正丁硫基、異丁硫基、第二丁硫基、第三丁硫基、正戊硫基、第二戊硫基、正己硫基、環己硫基、正庚硫基、環庚硫基、
正辛硫基、環辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、環戊烯硫基、己烯硫基、環己烯硫基、庚烯硫基、環庚烯硫基、辛烯硫基、環辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基。
根據本發明之一較佳實施態樣,該標號n等於0。
根據本發明之另一較佳實施態樣,該標號m等於0或1。
根據本發明之一特佳實施態樣,n等於0和m等於1。
根據本發明之另一較佳實施態樣,芳族環中最多三個
基團W等於N,特佳地芳族環中最多二個基團W等於N,及非常特佳地芳族環中最多一個基團W等於N。
此外較佳的是六員環中之不超過二個相鄰的基團W等於N。
尤佳的是W等於CR1。
根據另一較佳實施態樣,最多一個基團V等於N。
尤佳的是,V等於CR1。
根據一較佳實施態樣,X係選自N(R2)、O、C(R2)2、S,更佳地X為C(R2)2。
就基團Y而言,較佳的是環中之恰好二個或恰好三個基團Y等於N,且剩餘基團Y等於CR1。特佳的是環中之恰好三個基團Y等於N,且剩餘基團Y等於CR1。就基團Y而言,此外較佳的是不超過二個相鄰的基團Y等於N,特佳地沒有相鄰的基團Y等於N。
根據另一較實施態樣,表示CR1之基團Y中之基團R1彼此形成環。此等基團較佳為表示CR1之相鄰的基團Y中之基團R1。在此情形下,表示CR1之相鄰的基團Y中之基團R1特佳地形成縮合苯環。在此情形下,非常特佳的是恰好二個基團Y等於N。
就基團Ar4而言,較佳的是其表示下式(Ar4-I)之基團:
其中虛線表示至茚并咔唑基團及含有基團Y之六員環的
鍵,Ar5 在每次出現時相同或不同地為具有6至18個芳族環原子之芳基或雜芳基,其可經一或多個基團R1取代,其中R1係如上文所定義;及K 為1、2、3或4,其中選擇標號k以使整個基團Ar1中之芳族環原子的數目不超過數目40。
Ar5較佳地在每次出現時相同或不同地為具有6至14個芳族環原子之芳基或雜芳基,特佳地為具有6至10個芳族環原子之芳基或雜芳基,及非常特佳地為具有6個芳族環原子之芳基或雜芳基,其中該等基團可經一或多個基團R1取代。
根據一較佳實施態樣,在此基團R1在彼等所鍵結之芳基或雜芳基Ar5之間形成環。特佳地,表示苯基之兩個基團Ar5連結而形成茀基。
標號k較佳為1、2或3,更佳為1或2和特佳為1。
就基團Ar3而言,較佳的是其係選自具有6至30個芳族環原子,特佳地6至24個芳族環原子之芳族或雜芳族環系統,其可經一或多個基團R1取代。
這些當中,式(Y-1)為特佳。
基團R1較佳地在每次出現時相同或不同地為H、D、F、CN、Si(R3)3、N(R3)2、具有1至10個C原子之直鏈烷基或烷氧基或具有3至10個C原子之具支鏈或環狀烷基或烷氧基(其中上述基團可各自經一或多個基團R3取代且其中上述基團中之一或多個CH2基團可經-C≡C-、-R3C=CR3-、Si(R3)2、C=O、C=NR3、-NR3-、-O-、-S-、-C(=O)O-或-C(=O)NR3-置換)、或具有5至20個芳族環原子之芳族或雜芳族環系統,其在各情況下可經一或多個基團R3取代,其中位於Ar1上之二個相鄰的基團R1或位於Ar2上之二個相鄰的基團R1可彼此連接且可形成環。
基團R2較佳地在每次出現時相同或不同地為H、D、F、CN、Si(R3)3、N(R3)2、具有1至10個C原子之直鏈烷基或烷氧基或具有3至10個C原子之具支鏈或環狀烷基或烷氧基(其中上述基團可各自經一或多個基團R3取代且其中上述基團中之一或多個CH2基團可經-C≡C-、-R3C=CR3-、Si(R3)2、C=O、C=NR3、-NR3-、-O-、-S-、-C(=O)O-或-C(=O)NR3-置換)、或具有5至20個芳族環原子之芳族或雜芳族環系統,其在各情況下可經一或多個基團R3取代;其中二個基團R2可彼此連接且可形成環。
基團R3較佳地在每次出現時相同或不同地為H、D、
F、CN、Si(R4)3、N(R4)2、具有1至10個C原子之直鏈烷基或烷氧基或具有3至10個C原子之具支鏈或環狀烷基或烷氧基(其中上述基團可各自經一或多個基團R4取代且其中上述基團中之一或多個CH2基團可經-C≡C-、-R4C=CR4-、Si(R4)2、C=O、C=NR4、-NR4-、-O-、-S-、-C(=O)O-或-C(=O)NR4-置換);或具有5至20個芳族環原子之芳族或雜芳族環系統,其在各情況下可經一或多個基團R4取代,其中二或更多個基團R3可彼此連接且可形成環。
關於基團Ar4至式(1)中之咔唑的鍵結,較佳的是此鍵結位於下式(1-A)中以"a"和"b"表示之位置處,特佳位於以"a"表示之位置處。若標號m等於0,則對應情況適用於所鍵結二芳胺基基團(-NAr1Ar2)而非Ar4。
此外較佳地,式(1-1)和(1-6)中含有基團Y之六員環較佳符合上述式(Y-1)至(Y-6)中之一者,特佳符合式(Y-1)。
此外,較佳地,上述式中含有基團Y之六員環較佳符合上述式(Y-1)至(Y-6)中之一者,特佳符合式(Y-1)。
此外,上述式中含有基團Y之六員環較佳符合上述式(Y-1)至(Y-6)中之一者,特佳符合式(Y-1)。
此外,上述式中含有基團Y之六員環較佳符合上述式(Y-1)至(Y-6)中之一者,特佳符合式(Y-1)。
此外,上述式中含有基團Y之六員環較佳符合上述式(Y-1)至(Y-6)中之一者,特佳符合式(Y-1)。
式(1-1-3)至(1-6-3)和(1-1-4)至(1-6-4)之中,特佳者為式(1-1-3)和(1-1-4)。
根據本發明之一較佳實施態樣,基團Ar1和Ar2二者表示具有12至30個芳族C原子之芳族環系統、具有13至30個芳族環原子之雜芳基或具有10至20個芳族C原子之芳基,彼等各自可經一或多個基團R1取代。
根據本發明之另一較佳實施態樣,基團Ar1或Ar2中的至少一者係選自由下列所組成之群組:聯苯基、聯三苯基、聯四苯基、茀基、螺二茀基、咔唑基、二苯并呋喃基、二苯并噻吩基、萘基、蒽基(anthracyl)、菲基(phenantryl)、基、三伸苯基、芘基、苝基,彼等各自可經一或多個基團R3取代。
更佳地,基團Ar1和Ar2二者皆選自下列所組成之群組:聯苯基、聯三苯基、聯四苯基、茀基、螺二茀基、咔唑基、二苯并呋喃基、二苯并噻吩基、萘基、蒽基、菲基(phenantryl)、基、三伸苯基、芘基、苝基,彼等各自可經一或多個如上述所定義之基團R3取代。
非常特佳的是基團Ar1和Ar2皆選自式(11)至(77)之基團。
若式(1)、(1-1)至(1-6)、(1-1-1)至(1-6-1)、(1-1-2)至(1-6-2)、(1-1-3)至(1-6-3)和(1-1-4)至(1-6-4)或較佳實施態樣之化合物中的基團Ar1和Ar2彼此以基團E連接,則基團-NAr1Ar2較佳具有下式(78)至(85)中之一者的結構,更佳具有式(78)至(81)中之一者的結構:
特佳者為式(1)、(1-1)至(1-6)、(1-1-1)至(1-6-1)、(1-1-2)至(1-6-2)、(1-1-3)至(1-6-3)和(1-1-4)至(1-6-4)之化合物,其中上述較佳實施態樣同時出現。因此特佳者為化合物,其中:Y 為式(Y-1)至(Y-6)中之一者的基團;W 為CR1;X 為C(R2)2;Ar1、Ar2相同或不同地為式(10)至(77)中之一者的基團;或-NAr1Ar2表示式(78)至(81)中之一者的基團;R1 在每次出現時相同或不同地選自由下列所組成之
群組:H、D、F、CN、Si(R3)3、N(R3)2、具有1至10個C原子之直鏈烷基或烷氧基或具有3至10個C原子之支鏈或環狀烷基或烷氧基(其中上述基團各自可經一或多個基團R3取代且其中上述基團中之一或多個CH2基團可經-C≡C-、-R3C=CR3-、Si(R3)2、C=O、C=NR3、-NR3-、-O-、-S-、-C(=O)O-或-C(=O)NR3-置換)、或具有5至20個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R3取代),其中位於Ar1上之二個相鄰的基團R1或位於Ar2上之二個相鄰的基團R1可彼此連接且可形成環。
R2 在每次出現時相同或不同地選自由下列所組成之群組:H、D、F、CN、Si(R3)3、N(R3)2、具有1至10個C原子之直鏈烷基或烷氧基或具有3至10個C原子之支鏈或環狀烷基或烷氧基(其中上述基團各自可經一或多個基團R3取代且其中上述基團中之一或多個CH2基團可經-C≡C-、-R3C=CR3-、Si(R3)2、C=O、C=NR3、-NR3-、-O-、-S-、-C(=O)O-或-C(=O)NR3-置換)、或具有5至20個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R3取代);其中二個基團R2可彼此連接且可形成環。
R3 在每次出現時相同或不同地選自由下列所組成之群組:H、D、F、CN、Si(R4)3、N(R4)2、具有1
至10個C原子之直鏈烷基或烷氧基或具有3至10個C原子之支鏈或環狀烷基或烷氧基(其中上述基團各自可經一或多個基團R4取代且其中上述基團中之一或多個CH2基團可經-C≡C-、-R4C=CR4-、Si(R4)2、C=O、C=NR4、-NR4-、-O-、-S-、-C(=O)O-或-C(=O)NR4-置換、或具有5至20個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R4取代);其中二個基團R3可彼此連接且可形成環。
m 為0或1;n 為0。
可利用有機化學的已知合成步驟來製備根據本發明之
化合物。此等方法包括(例如)過渡金屬催化之偶合反應(例如鈴木(Suzuki)及布赫瓦爾德(Buchwald)偶合)、溴化及鹵化。
製備根據本發明之化合物的說明性方法呈現於下。所示方法特別適合於製備根據本發明之化合物。然而,可設想替代方法且在某些情形下可能為較佳。因此,熟習此項技術者將能夠在其一般專業知識之範圍內修改下示方法。
如流程1中所示較佳地合成根據本發明之化合物。流程1中之化合物可在自由位置處經任何所要有機基團R取代。
在此使茚并咔唑化合物在第一步驟中與含有缺電子雜芳基之鹵化芳基化合物進行反應。其中可製備此類型之茚并咔唑化合物的方式係從先前技術得知且藉由本申請案中之工作例予以闡釋。第一步驟較佳地係在布赫瓦爾德偶合之條件下進行。隨後對茚并咔唑骨架進行鹵化。此鹵化較佳為溴化,特佳地使用試劑NBS。
此步驟較佳接著鈴木偶合至帶有硼酸取代基之三芳基胺衍生物或此步驟較佳接著與二芳基胺衍生物之布赫瓦爾德偶合。
所得的產物可已表示目標化合物且符合式(1)。然而,可依照另外的步驟,例如為了進一步引入官能基團或基團。
因此本發明此外關於一種製備式(1)化合物之方法,其特徵在於使茚并咔唑化合物與含有缺電子雜芳基之芳族或雜芳族環系統反應,其中該芳族或雜芳族環系統係偶合至茚并咔唑之氮原子。該反應較佳為茚并咔唑和鹵化芳族或雜芳環系統之間的布赫瓦爾德偶合。
此外,反應產物較佳隨後被提供反應性官能團,例如藉由鹵化或藉由轉化成硼酸。此外,較佳接著進行鈴木偶
合至三芳胺基衍生物或布赫瓦爾德偶合至二芳胺基。
上述根據本發明之化合物,特別是經反應性脫離基(諸如溴、碘、氯、硼酸或硼酸酯)取代之化合物可用作製備對應寡聚物、樹枝狀聚合物或聚合物之單體。適當反應性脫離基為(例如)溴、碘、氯、硼酸、硼酸酯、胺、分別含有終端C-C雙鍵或參鍵之烯基或炔基、環氧乙烷、環氧丙烷、進行環加成作用(例如1,3-偶極環加成作用)之基團(諸如(例如)二烯或疊氮化物)、羧酸衍生物、醇和矽烷。
因此本發明此外關於包含一或多種式(1)之化合物的寡聚物、聚合物或樹枝狀聚合物,其中至聚合物、寡聚物或樹枝狀聚合物之鍵可定位於經R1或R2取代之式(1)中的任何所要位置處。視式(1)之化合物的連接而定,該化合物為寡聚物或聚合物的側鏈之部分或主鏈的部分。寡聚物就本發明的意義而言意指從至少3個單體單元建構之化合物。聚合物就本發明的意義而言意指從至少十個單體單元建構之化合物。根據本發明之聚合物、寡聚物或樹枝狀聚合物可為共軛、部分共軛或非共軛。根據本發明之寡聚物或聚合物可為直鏈、支鏈或樹枝狀。在以直鏈方式連接之結構中,式(1)之單元可彼此直接連接或經由二價基團(例如經由經取代或未經取代的伸烷基、經由雜原子或經由二價芳族或雜芳族基團)彼此連接。在支鏈及樹枝狀結構中,三個或多個式(1)之單元可(例如)經由三價或多價基團(例如經由三價或多價芳族或雜芳族
基團)連接,以產生支鏈或樹枝狀寡聚物或聚合物。
與上述針對式(1)之化合物相同的較佳選擇適用於寡聚物、樹枝狀聚合物及聚合物中的式(1)之重複單元。
為了製備寡聚物或聚合物,將根據本發明之單體進行均聚合或與其他單體進行共聚合。適合且較佳的共聚單體係選自菲(例如根據EP 842208或WO 00/22026)、螺二茀(例如根據EP 707020、EP 894107或WO 06/061181)、對-伸苯基(例如根據WO 92/18552)、咔唑(例如根據WO 04/070772或WO 2004/113468)、噻吩(例如根據EP 1028136)、二氫菲(例如根據WO 2005/014689或WO 2007/006383)、順式-和反式-茚并茀(例如根據WO 2004/041901或WO 2004/113412)、酮(例如根據WO 2005/040302)、菲(例如根據WO 2005/104264或WO 2007/017066)亦或多個此等單元。聚合物、寡聚物及樹枝狀聚合物通常亦含有其他單元,例如發光(螢光或磷光)單元,諸如,例如乙烯基三芳基胺(例如根據WO 2007/068325)或磷光金屬錯合物(例如根據WO 2006/003000)及/或電荷傳輸單元,特別是彼等以三芳基胺為主者。
根據本發明之聚合物和寡聚物通常藉由聚合一或多種類型之單體而製備,其之至少一種單體產生聚合物中的式(I)之重複單元。適當的聚合反應為熟習該項技術者已知的且描述於文獻中。產生C-C或C-N連接之特別適合
且較佳的聚合反應如下:(A)鈴木(SUZUKI)聚合;(B)山本(YAMAMOTO)聚合;(C)施蒂勒(STILLE)聚合;及(D)哈特維希-布赫瓦爾德(HARTWIG-BUCHWALD)聚合。
其中可藉由此等方法進行聚合之方式及其中可接著自反應介質分離聚合物且進行純化之方式為熟習此項技術者已知且詳細描述於文獻中,例如於WO 2003/048225、WO 2004/037887及WO 2004/037887中。
本發明因此亦關於一種製備根據本發明之聚合物、寡聚物和樹枝狀聚合物之方法,其特徵在於它們係藉由鈴木聚合、山本聚合、施蒂勒聚合或哈特維希-布赫瓦爾德聚合而製得。根據本發明之樹枝狀聚合物可藉由熟習該項技術者已知的方法或其類似方法製得。適合之方法說明於文獻中,諸如(例如)Frechet,Jean M.J.;Hawker,Craig J.,"Hyperbranched polyphenylene and hyperbranched polyesters:new soluble,three-dimensional,reactive polymers",Reactive & Functional Polymers(1995),26(1-3),127-36;Janssen,H.M.;Meijer,E.W.,"The synthesis and characterization of dendritic molecules",Materials Science and Technology(1999),20(Synthesis of Polymers),403-458;Tomalia,Donald A.,"Dendrimer molecules",Scientific American(1995),272(5),62-6;
WO 2002/067343 A1及WO 2005/026144 A1中。
為了從液相處理根據本發明之化合物(例如藉由旋轉塗佈或藉由印刷方法),需要根據本發明之化合物的調合物。此等調合物可為例如溶液、分散液或乳液。為此目的,較佳可為使用二或多種溶劑之混合物。適合且較佳的溶劑為(例如)甲苯、苯甲醚、鄰-、間-或對-二甲苯、苯甲酸甲酯、對稱三甲苯、四氫萘、藜蘆醚、THF、甲基-THF、THP、氯苯、二烷、苯氧基甲苯(特別是3-苯氧基甲苯)、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯啶酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、異丙苯、環己醇、環己酮、環己基苯、十氫萘、十二烷基苯、苯甲酸乙酯、茚烷、苯甲酸甲酯、NMP、對-異丙基甲苯、苯基乙基醚、1,4-二異丙基苯、二苯甲基醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二甲基醚、二乙二醇單丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-異丙基萘、戊基苯、己基苯、庚基苯、辛基苯、1,1-雙(3,4-二甲基苯基)乙烷或此等溶劑之混合物。
因此本發明此外關於一種調合物,特別是一種溶液、分散液或乳液,其包含至少一種式(1)之化合物或至少一種含有至少一種式(1)之單元的聚合物、寡聚物或樹枝狀聚合物及至少一種溶劑,較佳為有機溶劑。其中可製
備此類型之溶液的方式為熟習此項技術者已知且說明於(例如)WO 2002/072714、WO 2003/019694及其中所引用之文獻中。
式(1)之化合物適合用於電子裝置,特別是有機電致發光裝置(OLED)中。取決於取代,式(1)化合物可用於不同功能及層中。較佳者為用作發光層中之基質材料(特佳地與磷光發光體組合),及/或用作電子傳輸材料,及/或用作電洞阻擋材料。
因此本發明此外關於式(1)之化合物於電子裝置的用途。電子裝置在此較佳係選自由下列所組成之群組:有機積體電路(OIC)、有機場效電晶體(OFET)、有機薄膜電晶體(OTFT)、有機發光電晶體(OLET)、有機太陽能電池(OSC)、有機光學偵測器、有機感光器(photoreceptor)、有機場淬滅裝置(OFQD)、有機發光電化學電池(OLEC)、有機雷射二極體(O-雷射)及特佳為有機電致發光裝置(OLED)。
本發明此外關於包含至少一種式(1)化合物之電子裝置。電子裝置在此較佳係選自上述裝置。
特佳者為包含陽極、陰極及至少一個發光層之有機電致發光裝置,其特徵在於該裝置包含至少一個包括至少一種式(1)化合物之有機層。較佳者為包括陽極、陰極及至少一個發光層之有機電致發光裝置,其特徵在於該裝置中之至少一個層(選自發光層、電子傳輸層、電子注入層及電洞阻擋層)包含至少一種式(1)化合物。
電子傳輸層意指任一配置於陰極與發光層之間的具有電子傳輸性質之所要有機層。
電子注入層意指任一配置於陰極與發光層之間的具有電子注入性質且直接毗鄰陰極之所要有機層。
電洞阻擋層意指任一位於發光層和陰極之間且具有電洞阻擋性質之所要有機層。根據本申請案之電洞阻擋層較佳地位於發光層與電子傳輸層之間,特佳直接毗鄰陰極側上之發光層。電洞阻擋層之材料通常以低HOMO而區分。
除陰極、陽極及發光層之外,電子裝置亦可包含其他層。此等在各種情況下係選自例如一或多種電洞注入層、電洞傳輸層、電洞阻擋層、電子傳輸層、電子注入層、電子阻擋層、激子阻擋層、中間層、電荷產生層(IDMC 2003,Taiwan;Session 21 OLED(5),T.Matsumoto,T.Nakada,J.Endo,K.Mori,N.Kawamura,A.Yokoi,J.Kido,Multiphoton Organic EL Device Having Charge Generation Layer)及/或有機或無機p/n接面。然而,應指出:該等層中之各者不一定必須存在且層之選擇總是取決於所用化合物且特別是亦取決於電致發光裝置是否為螢光或磷光。
電子裝置之層順序較佳如下;
-陽極-
-電洞注入層-
-電洞傳輸層-
-隨意地另外電洞傳輸層-
-發光層-
-電子傳輸層-
-電子注入層-
-陰極-。
在此應再次指出,並非所有該等層必須存在,及/或可另外存在其他層。
根據本發明之電子裝置可包含多個發光層。在此情況下,此等發光層特佳具有總計多個在380nm與750nm之間的發光最大值,整體上導致為白色發光,即將能夠發螢光或磷光及發藍光或黃光或橘光或紅光的各種發光化合物使用於發光層中。特佳者為三層系統,亦即具有三個發光層之系統,其中此等層中之至少一者較佳包含至少一種式(I)化合物且其中該三層呈現藍色、綠色和橘色或紅色發光(基本結構參見例如WO 2005/011013)。根據本發明之化合物可替代地和/或另外也存在於電子傳輸層或另一層中。應注意:為了產生白光,單獨使用之在寬波長範圍發光的發光體化合物亦適合於代替多個發色之發光體化合物。
式(1)化合物較佳地存在於電子裝置中作為發光層中之基質材料,特佳地與一或多種磷光發光體化合物組合。發光體化合物較佳地呈摻雜劑之形式。
術語摻雜劑、基質材料及磷光發光體化合物在此係如上述所定義。
較佳地與式(1)化合物組合用作基質材料之發光體
化合物為下示磷光發光體化合物。
電子裝置之發光層亦可包含含有多種基質材料(混合基質系統)及/或多種摻雜劑之系統。亦在此情況下,摻雜劑通常為其比例在系統中為較小的材料及基質材料為其比例在系統中為較大的材料。然而,在個別的情況下,個別基質材料在系統中之比例可小於個別摻雜劑之比例。
在本發明之另一較佳實施態樣中,式(1)之化合物係用作混合-基質系統之成分。混合-基質系統較佳包含二或三種不同基質材料,特佳二種不同基質材料。二種材料中之一者在此較佳為具有電洞傳輸性質之材料且其他材料為具有電子傳輸性質之材料。然而,混合-基質成分之所要電子傳輸和電洞傳輸性質也可主要或完全組合於單一混合-基質成分中,其中另外混合-基質成分滿足其他功能。
二種不同基質材料在此可以1:50至1:1,較佳地1:20至1:1,特佳1:10至1:1及非常特佳地1:4至1:1的比率存在。混合-基質系統較佳地使用於磷光有機電致發光裝置中。對於混合-基質系統之更準確的資訊特別是於申請案WO 2010/108579中說明。
混合-基質系統可包含一或多種摻雜劑,較佳地一或多種磷光摻雜劑。通常,混合-基質系統較佳係使用於磷光有機電致發光裝置。
可與根據本發明之化合物組合用作混合-基質系統的基質成分之特別適合的基質材料係選自下示用於磷光摻雜劑之較佳基質材料或用於螢光摻雜劑之較佳基質材料,取
決於混合-基質系統中使用什麼類型之摻雜劑。
用於混合-基質系統中之較佳磷光摻雜劑為顯示於下表中的磷光摻雜劑。
根據本發明之電子裝置的發光層中之基質材料的比例就螢光發光層而言較佳係介於50.0和99.9體積%之間,特佳地介於80.0和99.5體積%之間及非常特佳地介於92.0和99.5體積%之間,並就磷光發光層而言係介於85.0與97.0體積%之間。對應地,摻雜劑的比例就螢光發光層而言較佳係介於0.1和50.0體積%之間,特佳地介於0.5和20.0體積%之間和非常特佳介於0.5和8.0體積%之間,並就磷光發光層而言係介於3.0與15.0體積%之間。
在本發明之另一較佳實施態樣中,式(1)化合物係用作電子傳輸層或電子注入層或電洞阻擋層中之電子傳輸材料。
較佳地存在於根據本發明之電子裝置的上述功能層中之材料係指示於下。
適當磷光發光體特別為在適當激發時發光(較佳在可見光區域內)且另外含有至少一種具有原子序大於20,較佳為大於38且少於84,特佳為大於56且少於80的原子之化合物。所使用之磷光發光體較佳為含有銅、鉬、鎢、錸、釕、鋨、銠、銥、鈀、鉑、銀、金或銪的化合物,特別是含有銥、鉑或銅的化合物。
所有發光銥、鉑或銅錯合物皆可視為就本發明意義而言之磷光化合物。
磷光發光體的實例係由申請案WO 2000/70655、WO 2001/41512、WO 2002/02714、WO 2002/15645、EP 1191613、EP 1191612、EP 1191614、WO 2005/033244、WO 2005/019373及US 2005/0258742揭示。通常,根據先前技術用於磷光OLED且為熟習有機電致發光裝置領域之技術者已知的所有磷光錯合物皆適合使用於根據本發明的裝置。
較佳螢光發光體係選自芳基胺之類別。芳基胺或芳族胺就本發明之意義而言意指含有三個經取代或未經取代之芳族或雜芳族環系統直接鍵結於氮之化合物。此等芳族或雜芳族環系統中之至少一者較佳為縮合環系統,特佳具有至少14個芳族環原子。其較佳例子為芳族蒽胺、芳族蒽二胺、芳族芘胺、芳族芘二胺、芳族胺或芳族二胺。芳族蒽胺意指其中一個二芳胺基與蒽基直接鍵結之化合物,較佳地在9-位置上。芳族蒽二胺意指其中二個二芳胺基與蒽基直接鍵結之化合物,較佳地在9,10-位置上。芳族芘胺、芘二胺、胺及二胺係與其類似地定義,其中二芳胺基較佳地在1-位置或1,6-位置上與芘鍵結。另外的較佳發光體化合物為茚并茀胺和茚并茀二胺(例如根據WO 2006/108497或WO 2006/122630)、苯并茚并茀胺和苯并茚并茀二胺(例如根據WO 2008/006449)、和二苯并茚并茀胺和二苯并茚并茀二胺(例如根據
WO 2007/140847)、和WO 2010/012328中所揭示的含有縮合芳基之茚并茀衍生物。同樣較佳者為WO 2012/048780和尚未公開EP 12004426.8中所揭示的芘芳基胺。同樣較佳者為尚未公開之EP 12006239.3中所揭示的苯并茚并茀胺。
除了根據本發明之化合物外,較佳用於螢光發光體之適當基質材料為選自各種種類之物質的材料。較佳基質材料係選自寡聚伸芳基(oligoarylene)(例如根據EP 676461之2,2’,7,7’-肆苯基螺二茀或二萘基蒽),特別是含有縮合芳族基團之寡聚伸芳基、寡聚伸芳基伸乙烯基(oligoarylenevinylene)(例如根據EP 676461之DPVBi或螺-DPVBi)、多牙(polypodal)金屬錯合物(例如根據WO 2004/081017)、電洞傳導化合物(例如根據WO 2004/058911)、電子傳導化合物,特別是酮、氧化膦、亞碸、等等(例如根據WO 2005/084081和WO 2005/084082)、阻轉異構物(例如根據WO 2006/048268)、硼酸衍生物(例如根據WO 2006/117052)或苯并蒽(例如根據WO 2008/145239)之種類。特佳基質材料係選自包含萘、蒽、苯并蒽及/或芘之寡聚伸芳基(oligarylene)或這些化合物的阻轉異構物、寡聚伸芳基伸乙烯基(oligoarylenevinylene)、酮、氧化膦和亞碸之種類。非常特佳的基質材料係選自包含蒽、苯并蒽、苯并菲及/或芘之寡聚伸芳基(oligoarylene)或這些化合物的阻轉異構物之種類。寡聚伸芳基(oligoarylene)就本發明之意
義而言意欲表示一種其中至少三個芳基或伸芳基彼此鍵結之化合物。此外較佳者為WO 2006/097208、WO 2006/131192、WO 2007/065550、WO 2007/110129、WO 2007/065678、WO 2008/145239、WO 2009/100925、WO 2011/054442和EP 1553154中所揭示之蒽衍生物和EP 1749809、EP 1905754及US 2012/0187826中所揭示之芘化合物。
除根據本發明之化合物外,用於磷光發光體之較佳基質材料為芳族胺(特別是三芳基胺(例如根據US 2005/0069729)、咔唑衍生物(例如CBP,N,N-雙咔唑基聯苯)或根據WO 2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527或WO 2008/086851之化合物、橋聯咔唑衍生物(例如根據WO 2011/088877和WO 2011/128017)、茚并咔唑衍生物(例如根據WO 2010/136109和WO 2011/000455)、氮雜咔唑衍生物(例如,根據EP 1617710、EP 1617711、EP 1731584、JP 2005/347160)、吲哚并咔唑衍生物(例如根據WO 2007/063754或WO 2008/056746)、酮(例如根據WO 2004/093207或WO 2010/006680)、氧化膦、亞碸和碸(例如根據WO 2005/003253)、寡聚伸苯基、雙極性基質材料(例如根據WO 2007/137725)、矽烷(例如根據WO 2005/111172)、氮硼呃(azaborole)或硼酸酯(例如根據WO 2006/117052)、三衍生物(例如根據WO 2010/015306、WO 2007/063754或WO 2008/056746)、鋅錯合
物(例如根據EP 652273或WO 2009/062578)、鋁錯合物(例如BAlq)、二氮矽呃(diazasilole)和四氮矽呃衍生物(例如根據WO 2010/054729)、和二氮磷呃(diazaphosphole)衍生物(例如根據WO 2010/054730)。
適當電荷傳輸材料當可用於根據本發明之有機電致發光裝置的電洞注入或電洞傳輸層或電子傳輸層中,為(例如)Y.Shirota等人,Chem.Rev.2007,107(4),953-1010中所揭示之化合物,或如根據先前技術用於此等層中之其他材料。
除根據本發明之化合物外,可用於電子傳輸層之材料為所有根據先前技術用作電子傳輸層中的電子傳輸材料之材料。特別適合的是鋁錯合物(例如Alq3)、鋯錯合物(例如Zrq4)、苯并咪唑衍生物、三衍生物、嘧啶衍生物、吡啶衍生物、吡衍生物、喹啉衍生物、喹啉衍生物、二唑衍生物、芳族酮、內醯胺、硼烷、二氮磷呃(diazaphosphole)衍生物及氧化膦衍生物。此外適合的材料為上述化合物之衍生物,如JP 2000/053957、WO 2003/060956、WO 2004/028217、WO 2004/080975和WO 2010/072300中所揭示。
可用於根據本發明之電致發光裝置中的電洞傳輸、電洞注入或電子阻擋層中之較佳電洞傳輸材料為茚并茀胺衍生物(例如根據WO 06/122630或WO 06/100896)、揭示於EP 1661888中之胺衍生物、六氮雜三伸苯基衍生物(例如根據WO 01/049806)、含有縮合芳族環之胺衍生
物(例如根據US 5,061,569)、揭示於WO 95/09147中之胺衍生物、單苯并茚并茀胺(例如根據WO 08/006449)、二苯并茚并茀胺(例如根據WO 07/140847)、螺二茀胺(例如根據WO 2012/034627或WO 2013/120577)、茀胺(例如根據尚未公開之申請案EP 12005369.9、EP 12005370.7及EP 12005371.5)、螺二苯并哌喃胺(例如根據WO 2013/083216)及二氫吖啶衍生物(例如根據WO 2012/150001)。
有機電致發光裝置之陰極較佳包含具有低功函數之金屬、金屬合金或包含各種金屬(諸如,例如鹼土金屬、鹼金屬、主族金屬或鑭系元素(例如Ca、Ba、Mg、Al、In、Mg、Yb、Sm、等等)之多層結構。亦適合的是包含鹼金屬或鹼土金屬和銀之合金,例如包含鎂和銀之合金。在多層結構之情況中,除該等金屬外,也可使用具有較高功函數之其他金屬,諸如,例如Ag或Al,在該情況中通常使用金屬之組合,諸如,例如Ca/Ag、Mg/Ag或Ag/Ag。較佳亦可於金屬陰極與有機半導體之間引入具有高介電常數之材料的薄中間層。適合於此目的者為(例如)鹼金屬氟化物或鹼土金屬氟化物,但對應氧化物或碳酸鹽(例如LiF、Li2O、BaF2、MgO、NaF、CsF、Cs2CO3、等等)亦適合。此外,喹啉酚鋰(LiQ)可使用於此目的。此層之厚度較佳係介於0.5和5nm之間。
陽極較佳包含具有高功函數之材料。陽極較佳具有相對於真空為大於4.5eV之功函數。適合於此目的者一方
面為具有高氧化還原電位之金屬,諸如(例如)Ag、Pt或Au。另一方面,金屬/金屬氧化物電極(例如Al/Ni/NiOx、Al/PtOx)亦可為較佳的。就一些應用而言,至少一個電極必須為透明或部分透明,以便促進有機材料之照射(有機太陽能電池)或光之耦合輸出(OLED、O-雷射)。較佳陽極材料在此為導電性混合金屬氧化物。特佳者為氧化銦錫(ITO)或氧化銦鋅(IZO)。此外較佳者為導電性摻雜型有機材料,特別為導電性摻雜型聚合物。此外,陽極也可由多層(例如ITO的內層和金屬氧化物(較佳氧化鎢、氧化鉬或氧化釩)的外層)組成。
將裝置適當地(視應用而定)結構化,配備接點且最後密封,因為在水及/或空氣存在下根據本發明之裝置的壽命會縮短。
在一較佳實施態樣中,根據本發明之電子裝置其特徵在於利用昇華方法塗佈一或多層,其中該等材料係於真空昇華單元中在低於10-5毫巴,較佳低於10-6毫巴之初壓力下藉由氣相沈積施加。然而,初壓力在此也可能甚至更低,例如低於10-7毫巴。
同樣較佳者為一種電子裝置,其特徵在於利用OVPD(有機氣相沉積)方法或輔以載體-氣體昇華法塗佈一或多層,其中該等材料係在介於10-5毫巴與1巴之間的壓力下施加。此方法的一特殊例子為OVJP(有機蒸氣噴墨印刷)法,其中該等材料係經由噴嘴直接施加且因此結構化(例如,M.S.Arnold等人,Appl.Phys.Lett.2008,92,
053301)。
此外較佳者為一種電子裝置,其特徵在於諸如(例如)以旋轉塗佈或利用任何所要印刷法(諸如,例如網版印刷、快乾印刷、噴嘴印刷或平版印刷,但是特佳為LITI(光誘導熱成像、熱轉移印刷)或噴墨印刷)從溶液製造一或多層。為此目的需要可溶性式(I)化合物。高溶解度可經由化合物的適當取代來達成。
為了製造根據本發明之電子裝置,此外較佳的是從溶液施加一或多層並藉由昇華方法施加一或多層。
根據本發明,包含一或多種式(I)化合物之電子裝置可用於顯示器中、作為照明應用中之光源及作為醫學及/或美容應用(例如光療法)中之光源。
下列工作例用於解釋本發明。彼等不意欲被解釋為限制性的。
除非另外指出,否則下列合成係在保護性氣體氛圍下於乾燥溶劑中進行。化合物(I)、(XIII)和(XII)可根據WO2010136109製備。化合物(II)、(XV)、(XVI)、(XX)、和(XXIV)為市售。化合物(IV)、(VI)和(XIII)可根據WO201155912製備。比較化合物(A)、(B)、和(C)可根據WO2010136109製備。(D)可根據WO2012014500A1製備。
實施例1:
化合物(V)的製備
製備化合物(V)的合成程序:
化合物(III)的製備
將在180mL的DMF中之20.0g(55.2mmol)的化合物(I)慢慢加至2.4g(60.7mmol,在油中之60%)的NaH在100mL的DMF中之懸浮液且在室溫下攪拌1h。將17.7g(66.4mmol)的化合物(II)溶解在80mL的DMF中並慢慢加至該懸浮液,及將反應混合物攪拌16h。將反應混合物倒在冰上,將有機相分離出來,用200mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物用乙醇洗滌,濾出及最後在減壓下乾燥。產量為28.2g(47.6mmol),對應於理論的78%。
化合物(V)的製備
將30.0g(50.6mmol)的化合物(III)、24.6g(55.8mmol)的化合物(IV)和5.8g(5.5mmol)的碳酸鈉懸浮於600mL的甲苯和220mL的水中。將590mg
(0.51mmol)的肆(三苯膦)鈀(0)加至此懸浮液,及將反應混合物在回流下攪拌16h。冷卻之後,將有機相分離出來,用300mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物用庚烷洗滌,濾出及最後在減壓下乾燥。產量為37.2g(40.9mmol),對應於理論的84%。
實施例2
化合物(VII)的製備
製備化合物(VII)的合成程序:
化合物(VII)的製備
將28.5g(48.1mmol)的化合物(III)、23.3g(52.9mmol)的化合物(VI)和5.5g(52.1mmol)的碳酸鈉懸浮於600mL的甲苯和220mL的水中。將0.56g(0.5mmol)的肆(三苯膦)鈀(0)加至此懸浮液,及將反應混合物在回流下攪拌16h。冷卻之後,將有機相分離出來,用300mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物從甲苯和庚烷再結晶。產量為21.7g(23.9mmol),對應於理論的50%。
實施例3
化合物(IX)的製備
製備化合物(IX)的合成程序:
將25g(42.1mmol)的化合物(VIII)、20.5g(52.9mmol)的化合物(IV)和4.8g(45.6mmol)的碳酸鈉懸浮於600mL的甲苯和220mL的水中。將0.42g(0.4mmol)的肆(三苯膦)鈀(0)加至此懸浮液,及將反應混合物在回流下攪拌16h。冷卻之後,將有機相分離出來,用300mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物從甲苯和庚烷再結晶。產量為26g(28.6mmol),對應於理論的68%。
實施例4
化合物(X)的製備
製備化合物(X)的合成程序:
化合物(X)的製備
將30g(50.5mmol)的化合物(VIII)、24.5g(55.6mmol)的化合物(VI)和5.8g(54.7mmol)的碳酸鈉懸浮於600mL的甲苯和220mL的水中。將0.58g(0.5mmol)的肆(三苯膦)鈀(0)加至此懸浮液,並將反應混合物在回流下攪拌16h。冷卻之後,將有機相分離出來,用300mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物從甲苯和庚烷再結晶。產量為27g(29.7mmol),對應於理論的64%。
實施例5
化合物(XIV)的製備
製備化合物(XIV)的合成程序:
化合物(XII)的製備
將30.0g(50.8mmol)的化合物(XI)懸浮在750mL的THF中。將12.6g(70.8mmol)的NBS慢慢加至此懸浮液,及將反應混合物在室溫下攪拌過夜。以水將反應混合物淬滅。將有機相分離出來,用300mL的二氯甲
烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物從再甲苯結晶。產量為21.6g(32.2mmol),對應於理論的63%。
化合物(XIV)的製備
將20g(29.9mmol)的化合物(III)、14.5g(32.9mmol)的化合物(VIII)和3.4g(32.4mmol)的碳酸鈉懸浮於600mL的甲苯和220mL的水中。將0.35g(0.3mmol)的肆(三苯膦)鈀(0)加至此懸浮液,及將反應混合物在回流下攪拌16h。冷卻之後,將有機相分離出來,用300mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物從甲苯和庚烷再結晶。產量為18g(18.3mmol),對應於理論的61%。
實施例6
化合物(XIX)的製備
製備化合物(XIX)的合成程序:
化合物(XVII)的製備
將34.7g(153.5mmol)的化合物(XV)、35.0g(153.5mmol)的化合物(XVI)和17.9g(168.8mmol)的碳酸鈉懸浮於120mL的甲苯、300mL的二烷和300mL的水中。將1.8g(1.5mmol)的肆(三苯膦)鈀(0)加至此懸浮液,及將反應混合物在110℃加熱16h。冷卻之後,將有機相分離出來,用300mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物從甲苯和庚烷再結晶。產量為32g(85.6mmol),對應於理論的56%。
化合物(XVIII)的製備
將在180mL的DMF中之20.0g(55.2mmol)的化合物(I)慢慢加至2.4g(60.7mmol,在油中之60%)的NaH在100mL的DMF中之懸浮液,並在室溫下攪拌1h。將24.8g(66.4mmol)的化合物(II)溶解在80mL
的DMF中並慢慢加至該懸浮液,及將反應混合物攪拌16h。將反應混合物倒在冰上,將有機相分離出來,用200mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物用乙醇洗滌,濾出及最後在減壓下乾燥。產量為29g(41.4mmol),對應於理論的75%。
化合物(XIX)的製備
將20g(28.6mmol)的化合物(VIII)、13.8g(31.5mmol)的化合物(IV)和3.3g(31mmol)的碳酸鈉懸浮於600mL的甲苯和220mL的水中。將0.33g(0.3mmol)的肆(三苯膦)鈀(0)加至此懸浮液,及將反應混合物在回流下攪拌16h。冷卻之後,將有機相分離出來,用300mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物從甲苯和庚烷再結晶。產量為18g(17.7mmol),對應於理論的62%。
實施例7
化合物(XXIII)的製備
製備化合物(XXIII)的合成程序:
化合物(XXI的製備)
將50.8g(186.0mmol)的化合物(XV)在580mL的THF中之溶液加至4.5g(185.1mmol)的Mg屑並將反應混合物攪拌16h。在0℃將反應混合物加至35.0g(154.8mmol)的化合物(XX)在190mL的THF中之溶液。將反應混合物慢慢升溫至室溫。24h之後,以12%之HCl水溶液將反應混合物淬滅,接著將有機相分離出來,用500mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。藉由管柱層析法在矽膠上使用二氯甲烷/庚烷的混合物(1/5)純化殘餘物。產量為24g(62.5mol),對應於理論的40%。
化合物(XXII)的製備
將在180mL的DMF中之20.0g(55.2mmol)的化合物(I)慢慢加至2.4g(60.7mmol,在油中之60%)的NaH在100mL的DMF中之懸浮液,並在室溫下攪拌1
h。將25.4g(66.3mmol)的化合物(XXI)溶解在80mL的DMF中並慢慢加至該懸浮液,及將反應混合物攪拌16h。將反應混合物倒在冰上,將有機相分離出來,用200mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物用乙醇洗滌,濾出及最後在減壓下乾燥。產量為30g(42.3mmol),對應於理論的77%。
化合物(XXIII)的製備
將20g(28.21mmol)的化合物(XXII)、3.7g(31.0mmol)的化合物(VI)和3.23g(30.5mmol)的碳酸鈉懸浮於600mL的甲苯和220mL的水中。將0.33g(0.3mmol)的肆(三苯膦)鈀(0)加至此懸浮液,及將反應混合物在回流下攪拌16h。冷卻之後,將有機相分離出來,用300mL的二氯甲烷萃取三次,在硫酸鎂上乾燥及隨後蒸發至乾燥。將殘餘物從甲苯和庚烷再結晶。產量為21g(20.5mmol),對應於理論的72%。
實施例8
化合物(XXV)的製備
製備化合物(XXV)的合成程序:
化合物(XXV)的製備
在Ar氛圍下將30.0g(50.6mmol)的化合物(VIII)和16.8g(50.6mmol)的化合物(XXIV)懸浮於500mL的甲苯中。將226mg(1.0mmol)的Pd(OAc)2加至燒瓶並在Ar氛圍下攪拌,接著將2.0mL的1M三-第三丁基膦溶液和7.3g(75.5mmol)的第三丁醇鈉加至燒瓶。將反應混合物在回流下攪拌24h。冷卻之後,將有機相分離出來,用200mL的水洗滌三次,在硫酸鎂上乾燥,過濾及隨後蒸發至乾燥。藉由管柱層析法在矽膠上使用乙酸乙酯/庚烷的混合物(1:3)純化殘餘物。產量為33.0g(39.6mmol),對應於理論的78%。
實施例9至12
溶液加工之OLED裝置的製備
有關本發明之化合物可從溶液加工以製造具有良好的性能之簡單OLED裝置。此等溶液加工之OLED裝置的製備類似於聚合物發光二極體(PLED)的製備,其已被廣泛地描述在文獻中(例如WO 2004/037887中之實施例)。在此情況,將根據本發明之化合物(V)、
(VII)、(IX)、(X)、(XIV)、(XIX)、(XXIII)和(XXV)溶解在甲苯中。該等溶液的典型固體含量係介於16和25g/L之間,以藉由旋塗達到典型裝置的80nm之層厚度。OLED裝置顯示下列結構:ITO/PEDOT:PSS/中間層/EML/陰極,其中EML為發光層。發光層(EML)不僅包括關於本發明之化合物(V)、(VII)、(IX)、(X)、(XIV)、(XIX)、(XXIII)和(XXV),其存在濃度為80wt%,但亦包括摻雜劑,TEG-001(由Merck市售的),其存在濃度為20%。結構化ITO基板及用於所謂的緩衝層之材料(PEDOT,實際為PEDOT:PSS)為市售(Technoprint and others之ITO,PEDOT:PSS呈來自HC Starck之水分散液Clevios Baytron® P。中間層用於電洞注入;在此情況下,使用HIL-012(由Merck市售的)。HIL-012為一種由以下單體組成的聚合物:
在惰性氣體,在此情況下為氬氣氛圍,旋塗發光層及在120℃下加熱10分鐘。最後,在真空中蒸發鋇和鋁之
陰極。發光層和陰極之間,也可蒸發電洞阻擋層及/或電子傳輸層。且中間層可由一或多個層來代替。
該裝置係藉由標準方法示性且OLED實施例尚未最佳化。
有關本發明的化合物和比較例之結構。
實施例9
從結果可知,用有關本發明之化合物IX製造的簡單溶液加工之OLED裝置的性能(特別是效率、壽命和電壓)比用比較化合物A獲得者更好。
實施例10
從結果可知,用有關本發明之化合物XIV製造的簡單溶液加工之OLED裝置的性能(特別是效率、壽命和電壓)比用比較化合物B獲得者更好。
實施例11
從結果可知,用有關本發明之化合物XXV製造的簡單溶液加工之OLED裝置的性能(特別是效率、壽命和電
壓)比用比較化合物C獲得者更好。
實施例12
從結果可知,用有關本發明之化合物VII、X、XIV和XIX製造的簡單溶液加工之OLED裝置的性能(特別是效率、壽命和電壓)比用比較化合物D獲得者更好。
Claims (16)
- 一種式(1-1)之化合物,
- 根據申請專利範圍第1項之化合物,其中該標號m等於1。
- 根據申請專利範圍第1項之化合物,其中該標號n等於0。
- 根據申請專利範圍第1至3項中任一項之化合物,其中W等於CR1。
- 根據申請專利範圍第1至3項中任一項之化合物,其中X等於C(R2)2。
- 根據申請專利範圍第1至3項中任一項之化合物,其中在環中恰好三個基團Y等於N,和其餘基團Y等於CR1。
- 一種寡聚物、聚合物或樹枝狀聚合物,其含有一或多種根據申請專利範圍第1至9項中之一或多項之化合物,其中至該聚合物、寡聚物或樹枝狀聚合物的鍵可定位於經R1或R2取代之式(1-1)中的任何所要位置。
- 一種調合物,其包含至少一種根據申請專利範圍第1至9項中之一或多項之化合物或至少一種根據申請專利範圍第10項之聚合物、寡聚物或樹枝狀聚合物及至少一種溶劑。
- 一種電子裝置,其係選自有機積體電路(OIC)、有機場效電晶體(OFET)、有機薄膜電晶體(OTFT)、有機發光電晶體(OLET)、有機太陽能電池(OSC)、有機光學偵測器、有機感光器(photoreceptor)、有機場淬滅裝置(OFQD)、有機發光電化學電池(OLEC)、有機雷射二極體(O-雷射)及有機電致發光裝置(OLED),其特徵在於其包含至少一種根據申請專利範圍第1至9項中之一或多項之化合物。
- 根據申請專利範圍第12項之電子裝置,其係選自有機電致發光裝置,其特徵在於其包含陽極、陰極和至少一種發光層,其中該裝置中之至少一層(選自發光層、電子傳輸層、電子注入層和電洞阻擋層)包含至少一種根據申請專利範圍第1至9項中之一或多項之化合物。
- 根據申請專利範圍第13項之電子裝置,其中根據申請專利範圍第1至9項中之一或多項之化合物係與一或多種磷光發光體化合物組合存在於發光層中。
- 一種用於製備根據申請專利範圍第1至9項中之一或多項之化合物之方法,其特徵在於使茚并咔唑化合物與含有缺電子雜芳基之芳族或雜芳族環系統反應,其中該芳族或雜芳族環系統係偶合至茚并咔唑之氮原子。
- 一種根據申請專利範圍第1至9項中之一或多項之化合物用在電子裝置之用途。
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-
2016
- 2016-01-07 CN CN201680006177.XA patent/CN107108578A/zh active Pending
- 2016-01-07 EP EP16700236.9A patent/EP3250658B1/en active Active
- 2016-01-07 KR KR1020177023964A patent/KR102626977B1/ko active IP Right Grant
- 2016-01-07 WO PCT/EP2016/000011 patent/WO2016119992A1/en active Application Filing
- 2016-01-07 JP JP2017540608A patent/JP6827938B2/ja active Active
- 2016-01-07 US US15/547,281 patent/US20180006237A1/en not_active Abandoned
- 2016-01-27 TW TW105102516A patent/TWI705062B/zh active
Also Published As
Publication number | Publication date |
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TW201700470A (zh) | 2017-01-01 |
CN107108578A (zh) | 2017-08-29 |
WO2016119992A1 (en) | 2016-08-04 |
KR102626977B1 (ko) | 2024-01-19 |
JP6827938B2 (ja) | 2021-02-10 |
JP2018507194A (ja) | 2018-03-15 |
EP3250658A1 (en) | 2017-12-06 |
US20180006237A1 (en) | 2018-01-04 |
EP3250658B1 (en) | 2019-06-19 |
KR20170110641A (ko) | 2017-10-11 |
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