JP6983754B2 - 有機エレクトロルミネッセンス素子のための材料 - Google Patents
有機エレクトロルミネッセンス素子のための材料 Download PDFInfo
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- JP6983754B2 JP6983754B2 JP2018504651A JP2018504651A JP6983754B2 JP 6983754 B2 JP6983754 B2 JP 6983754B2 JP 2018504651 A JP2018504651 A JP 2018504651A JP 2018504651 A JP2018504651 A JP 2018504651A JP 6983754 B2 JP6983754 B2 JP 6983754B2
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- 239000000463 material Substances 0.000 title claims description 31
- 238000005401 electroluminescence Methods 0.000 title claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 124
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- -1 alkoxy Motoma Chemical compound 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000011159 matrix material Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- 230000005525 hole transport Effects 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 229910005965 SO 2 Inorganic materials 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 12
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- 125000001424 substituent group Chemical group 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
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- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical group C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
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- 125000005842 heteroatom Chemical group 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
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- 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 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
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- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- 125000005259 triarylamine group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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- IGHOZKDBCCFNNC-UHFFFAOYSA-N 1h-imidazole;quinoxaline Chemical compound C1=CNC=N1.N1=CC=NC2=CC=CC=C21 IGHOZKDBCCFNNC-UHFFFAOYSA-N 0.000 description 2
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- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
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- 150000004696 coordination complex Chemical class 0.000 description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
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- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
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- 125000000623 heterocyclic group Chemical group 0.000 description 2
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical class C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
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- 238000004020 luminiscence type Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-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
- 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
- 238000007645 offset printing Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical class C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines 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
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 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
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 229940078162 triadine Drugs 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000006617 triphenylamine group Chemical class 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-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
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000012808 vapor phase Substances 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
Classifications
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Description
ArNは、以下の式(2−1)〜(2−3)の一つ基であり;
Xは、B(R0)、C(R0)2、Si(R0)2、C=O、C=NR0、C=C(R0)2、O、S、S=O、SO2、N(R0)、P(R0)およびP(=O)(R0)より成る基から選ばれる2価ブリッジであるか、
またはXは、以下の式(3)の基であり、
R0は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CHO、CN、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、NO2、Si(R8)3、B(OR8)2、OSO2R8、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルキル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基(夫々は、1以上の基R8により置換されてよく、各場合に、1以上の隣接しないCH2基は、R8C=CR8、C≡C、Si(R8)2、Ge(R8)2、Sn(R8)2、C=O、C=S、C=Se、P(=O)(R8)、SO、SO2、O、SもしくはCONR8で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)、各場合に、1以上の基R8により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R8で置換されてよい5〜40個の芳香族環原子を有するアリールオキシ基より成る基から選ばれ;ここで、同じCもしくはSi原子に結合する2個の置換基R0は、1以上の基R8により置換されてよいモノあるいはポリ環状の脂肪族環構造を随意に形成してもよく;ただし、2個のR0が、同じC原子に結合する場合には、少なくとも一つのR0は、H、D、F、CN、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルキル基または3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基(夫々は、1以上の基R4により置換されてよい。)より成る基から選ばれ;
R1、R2、R3、R4、R6またはR7は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CHO、CN、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、NO2、Si(R8)3、B(OR8)2、OSO2R8、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルキル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基(夫々は、1以上の基R8により置換されてよく、各場合に、1以上の隣接しないCH2基は、R8C=CR8、C≡C、Si(R8)2、Ge(R8)2、Sn(R8)2、C=O、C=S、C=Se、P(=O)(R8)、SO、SO2、O、SもしくはCONR8で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)、各場合に、1以上の基R8により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R8で置換されてよい5〜40個の芳香族環原子を有するアリールオキシ基より成る基から選ばれ;ここで、2個以上の隣接する置換基R1、2個以上の隣接する置換基R2、2個以上の隣接する置換基R3、2個以上の隣接する置換基R4、2個以上の隣接する置換基R6もしくは2個以上の隣接する置換基R7は、1以上の基R8により置換されてよいモノあるいはポリ環状の脂肪族環構造もしくは芳香族環構造を随意に形成してもよく;
R5は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CHO、CN、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、NO2、Si(R8)3、B(OR8)2、OSO2R8、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルキル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基(夫々は、1以上の基R8により置換されてよく、各場合に、1以上の隣接しないCH2基は、R8C=CR8、C≡C、Si(R8)2、Ge(R8)2、Sn(R8)2、C=O、C=S、C=Se、P(=O)(R8)、SO、SO2、O、SもしくはCONR8で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)より成る基から選ばれ;ここで、2個以上の隣接する置換基R5は、1以上の基R8により置換されてよいモノあるいはポリ環状の脂肪族環構造を随意に形成してもよく;
R8は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルキル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基(各場合に、1以上の隣接しないCH2基は、SO、SO2、O、Sで置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、BrもしくはIで置き代えられてよい。)、6〜60個のC原子を有する芳香族もしくは複素環式芳香族環構造より成る基から選ばれ; 2個以上の隣接する置換基R8は、モノもしくはポリ環状の脂肪族環構造を随意に形成してもよく;
Ar1、Arsは、出現毎に同一であるか異なり、各場合に、1以上の基R8により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
t、uは、同一であるか異なり、0または1であり;
m、n、q、rは、同一であるか異なり、0、1、2、3または4であり;ここで、t+m≦4およびu+n≦4であり;
pは、0、1または2であり;
iは、0、1または2であり;ここで、i=0またはj=0は、基Arsが存在せず、単結合により置き代えられることを意味し;
jは、1、2または3であり;
sは、0、1、2、3、4または5である。
好ましい態様によれば、基ArNは、以下の式(20)〜(84)の基から選ばれる;
a)古典的スピロ合成
したがって、本発明は、さらに、ジアリールアミノ基が、ジアリールアミン化合物とハロゲン化スピロビフルオレン化合物との間のC-Nカップリング反応により導入されることを特徴とする、式(1)の化合物の製造方法に関する。
(A)スズキ重合;
(B)ヤマモト重合;
(C)スチル重合および
(D)ハートウイッグ-ブッフバルト重合。
A)合成例
以下の合成を、別段の指定がない限り、保護ガス雰囲気下で実施する。出発材料を、ALDRICHまたはABCRから購入できる。文献から知られている出発材料の場合、角括弧内の数値は、対応するCAS番号である。
1,1’-ビス(ジフェニルホスフィノ)フェロセン(1.5g、2.7ミリモル)と、酢酸パラジウム(616mg、2.7ミリモル)と、ナトリウムtert-ブトキシド(22.9g、238ミリモル)とを、脱気トルエン(400ml)中、フェニル-アミン(17.0g、183ミリモル)と、2-ブロモ-9,9-ジメチル-9H-フルオレン(50.0g、183ミリモル)とに添加し、混合物を還流下で20時間、加熱する。反応混合物を室温まで冷まし、トルエンで増量し、セライトを通して濾過する。濾過物を水で増量し、トルエンで再抽出し、結合した有機相を脱水させ、真空で蒸発させる。残留物をシリカゲル(ヘプタン/ジクロロメタン)を通して濾過し、イソプロパノールから結晶化させる。フェニル-(9,9-ジメチル-9H-フルオレン-2-イル)アミンが、淡黄色の固形物の形態で得られる(40.9g、理論値の95%)。
トリ-tert-ブチルホスフィン(トルエン中4.4mlの1.0M溶液、4.4ミリモル)と、酢酸パラジウム(248mg、1.1ミリモル)と、ナトリウムtert-ブトキシド(16.0g、166ミリモル)とを、脱気トルエン(500ml)中、フェニル-(9,9-ジメチル-9H-フルオレン-2-イル)アミン(40.0g、140ミリモル)と、4-ブロモ-9,9’-スピロビフルオレン(56.9g、144ミリモル)とに添加し、混合物を還流下で2時間、加熱する。反応混合物を室温まで冷まし、トルエンで増量し、セライトを通して濾過する。濾過物を真空で蒸発させ、残留物を酢酸エチル/ヘプタンから結晶化させる。粗生成物をソックスレー抽出器中で抽出し(トルエン)、真空で二回、ゾーン昇華により精製する(p=3×10-4mbar、T=298℃)。生成物は淡黄色の固形物の形態で単離される(20.4g、理論値の24%、HPLCによる純度>99.99%)。
a)ビフェニル-4-イル-(9,9-ジメチル-9H-フルオレン-2-イル(4,4,5,5テトラメチル-[1,3,2]ジオキサボロラン-2-イル)-フェニル]-アミンの合成
本発明によるOLEDと先行技術にしたがうOLEDとが、WO 2004/058911にしたがう一般的プロセスにより製造されるが、ここに記載される状況(層厚の変化、材料)に適合される。
特に、本発明による化合物は、OLEDで、HIL、HTLまたはEBLとして適している。これらは、単層としてのみならず、HIL、HTL、EBLとしての混合成分として、またはEML内で適している。参照材料を含む素子(HTMV1、HTMV2、HTMV3)と比べて、本発明の化合物を含む試料は、より高い効率と、さらに著しく改善された寿命との両者を示す。これらは一重項青色とさらに三重項緑色のOLED素子の両者で試験された。
Claims (17)
- 式(1)の化合物;
ArNは、以下の式(2−1)または(2−2)の一つ基であり;
Xは、式(2−1)の場合には、C(R0) 2 、O、S、S=O、SO 2 より成る基から選ばれる2価ブリッジであるか、
Xは、式(2−2)の場合には、C(R0)2、O、S、S=O、SO 2 より成る基から選ばれる2価ブリッジであるか、
またはXは、以下の式(3)の基であり、
R0は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、1〜40個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基または、各場合に、1以上の基R8により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R8で置換されてよい5〜40個の芳香族環原子を有するアリールオキシ基より成る基から選ばれ; ただし、2個のR0が、同じC原子に結合する場合には、そこで、少なくとも一つのR0は、H、D、F、1〜40個のC原子を有する直鎖アルキルもしくはアルコキシ基または3〜40個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基より成る基から選ばれ;
R1、R2、R3またはR4は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、1〜40個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜40個のC原子を有する分岐アルキルもしくはアルコキシ基または、各場合に、1以上の基R8により置換されてよい5〜40個の芳香族環原子を有する芳香族環構造、1以上の基R8で置換されてよい5〜40個の芳香族環原子を有するアリールオキシ基より成る基から選ばれ;
R5は、出現毎に同一であるか異なり、H、D、F、CN、1〜10個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜10個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基(夫々は、1以上の基R8により置換されてよい。)より成る基から選ばれ;
R6は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、1〜40個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基または、各場合に、1以上の基R8により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R8で置換されてよい5〜40個の芳香族環原子を有するアリールオキシ基より成る基から選ばれ;
R7は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、1〜40個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基または、各場合に、1以上の基R8により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R8で置換されてよい5〜40個の芳香族環原子を有するアリールオキシ基より成る基から選ばれ;
R8は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、1〜40個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基または、6〜60個のC原子を有する芳香族もしくは複素環式芳香族環構造より成る基から選ばれ;
Arsは、出現毎に同一であるか異なり、各場合に、1以上の基R8により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
t、uは、同一であるか異なり、0または1であり;
m、n、q、rは、同一であるか異なり、0、1、2、3または4であり;ここで、t+m≦4およびu+n≦4であり
pは、0、1または2であり;
iは、0、1または2であり;ここで、i=0は、基Arsが存在せず、単結合により置き代えられることを意味し;
jは、1であり;
sは、0、1、2、3、4または5である。 - t+u=0または1であることを特徴とする、請求項1記載の化合物。
- 添え字iは、0であることを特徴とする、請求項1または2記載の化合物。
- R1〜R4は、出現毎に同一であるか異なり、Hから選ばれることを特徴とする、請求項1〜7何れか1項記載の化合物。
- R6とR7は、出現毎に同一であるか異なり、Hから選ばれることを特徴とする、請求項1〜8何れか1項記載の化合物。
- R0は、出現毎に同一であるか異なり、H、1〜10個のC原子を有する直鎖アルキル基、3〜10個のC原子を有する分岐あるいは環状アルキル基(夫々は、1以上の基R8により置換されてよい。)より成る基から選ばれることを特徴とする、請求項1〜9何れか1項記載の化合物。
- ジアリールアミノ基が、ジアリールアミン化合物とハロゲン化スピロビフルオレン化合物との間のC-Nカップリング反応により導入されることを特徴とする、請求項1〜10何れか1項記載の化合物の製造方法。
- 請求項1〜10何れか1項記載の少なくとも一つの化合物と少なくとも一つの溶媒を含む、調合物。
- 請求項1〜10何れか1項記載の化合物の電子素子での使用。
- 電子素子が有機エレクトロルミッセンス素子である請求項13記載の使用。
- 請求項1〜10何れか1項記載の少なくとも一つの化合物を含む電子素子。
- 電子素子が、有機エレクトロルミネッセンス素子、有機集積回路、有機電界効果トランジスタ、有機薄膜トランジスタ、有機発光トランジスタ、有機ソーラーセル、染料感受性有機ソーラーセル、有機光学検査器、有機光受容器、有機電場消光素子、発光電子化学セル、有機レーザーダイオードおよび有機プラスモン発光素子より成る群から選ばれる、請求項15記載の電子素子。
- 請求項1〜10何れか1項記載の化合物が、正孔輸送もしくは正孔注入もしくは励起子ブロッックもしくは電子ブロッック層中で正孔輸送材料として、または、蛍光もしくは燐光エミッターのためのマトリックス材料として用いられることを特徴とする、有機エレクトロルミネッセンス素子である請求項16記載の電子素子。
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EP3328825B1 (en) | 2023-06-28 |
JP2018529644A (ja) | 2018-10-11 |
EP3328825A1 (en) | 2018-06-06 |
CN107922312B (zh) | 2021-05-25 |
WO2017016632A1 (en) | 2017-02-02 |
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CN107922312A (zh) | 2018-04-17 |
KR20180031770A (ko) | 2018-03-28 |
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CN113248392B (zh) | 2024-04-16 |
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