JP6644688B2 - 電子素子のための材料 - Google Patents
電子素子のための材料 Download PDFInfo
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- JP6644688B2 JP6644688B2 JP2016539144A JP2016539144A JP6644688B2 JP 6644688 B2 JP6644688 B2 JP 6644688B2 JP 2016539144 A JP2016539144 A JP 2016539144A JP 2016539144 A JP2016539144 A JP 2016539144A JP 6644688 B2 JP6644688 B2 JP 6644688B2
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- 239000000463 material Substances 0.000 title claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 159
- 125000003118 aryl group Chemical group 0.000 claims description 113
- 125000004432 carbon atom Chemical group C* 0.000 claims description 91
- 239000011159 matrix material Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000005859 coupling reaction Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- DYMHCFPNCIRZBV-UHFFFAOYSA-N C12=CC=CC=C2C2(C3=CC=CC=C3C3=CC=CC=C32)C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 Chemical group C12=CC=CC=C2C2(C3=CC=CC=C3C3=CC=CC=C32)C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 DYMHCFPNCIRZBV-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000005259 triarylamine group Chemical group 0.000 claims description 5
- 230000005669 field effect Effects 0.000 claims description 3
- 238000007689 inspection Methods 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 239000010410 layer Substances 0.000 description 135
- -1 NR 9 Inorganic materials 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 230000005525 hole transport Effects 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 16
- 239000002019 doping agent Substances 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 229910052794 bromium Inorganic materials 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 13
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 229910052740 iodine Inorganic materials 0.000 description 12
- 239000000412 dendrimer Substances 0.000 description 11
- 229920000736 dendritic polymer Polymers 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 229910052710 silicon Inorganic materials 0.000 description 11
- 125000004001 thioalkyl group Chemical group 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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 0 C=*c1ccc(Cc2ccccc2-2)c-2c1 Chemical compound C=*c1ccc(Cc2ccccc2-2)c-2c1 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 7
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 7
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000005553 heteroaryloxy group 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
- 229910052709 silver Inorganic materials 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 125000004986 diarylamino group Chemical group 0.000 description 5
- 125000004475 heteroaralkyl group Chemical group 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000005577 anthracene group Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 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
- 150000002148 esters Chemical class 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-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
- 239000013074 reference sample Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 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 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 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 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- XJHCXCQVJFPJIK-UHFFFAOYSA-M cesium fluoride Substances [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 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
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-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
- 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 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- DRKHIWKXLZCAKP-UHFFFAOYSA-N 1-bromo-2-(2-bromophenyl)benzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1Br DRKHIWKXLZCAKP-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
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-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
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 101100293593 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nar-1 gene Proteins 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000006254 arylation reaction Methods 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/156—Hole transporting layers comprising a multilayered structure
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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- 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
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- 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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- H—ELECTRICITY
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Description
Arsは、出現毎に同一であるか異なり、各場合に、1以上の基R7により置換されてよい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であり;ここで、Arsは、基Eにより、Ar1および/またはAr2に連結してよく;
Ar1、Ar2は、出現毎に同一であるか異なり、各場合に、1以上の基R7により置換されてよい6〜60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、ここで、Ar1とAr2は、互いに連結してよく、および/または基Eにより、Ar1は、Arsに連結してよく、および/またはAr2は、Arsに連結してよく;
Eは、出現毎に同一であるか異なり、C(R7)2、O、SおよびNR7より成る基から選ばれ;
R1、R2、R3、R4、R5、R6は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、Si(R9)3、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、1以上の基R9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、Si(R9)2、C=NR9、P(=O)(R9)、SO、SO2、NR9、O、SもしくはCONR9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。)、または各場合に、1以上の基R9により置換されてよい6〜60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、または、1以上の基R9により置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または、各場合に1以上の基R9により置換されてよい5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル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または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または2個以上の隣接する置換基R5または2個以上の隣接する置換基R6は、1以上の基R9により置換されてよいモノあるいはポリ環式の脂肪族もしくは芳香族環構造を随意に形成してよく;
R7は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、Si(R9)3、N(R9)2、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、1以上の基R9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、Si(R9)2、C=NR9、P(=O)(R9)、SO、SO2、NR9、O、SもしくはCONR9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。)、または各場合に、1以上の基R9により置換されてよい6〜60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、または、1以上の基R9により置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または、各場合に1以上の基R4により置換されてよい5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル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R7は、1以上の基R9により置換されてよいモノあるいはポリ環式の脂肪族もしくは芳香族環構造を随意に形成してよく;
R8は、H、D、F、Cl、Br、I、CN、Si(R9)3、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、1以上の基R9により置換されてよく、1以上の隣接しないCH2基は、Si(R9)2、C=NR9、P(=O)(R9)、SO、SO2、NR9、O、SもしくはCONR9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。)、または各場合に、1以上の基R9により置換されてよい6〜60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、または、1以上の基R9により置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または、各場合に1以上の基R4により置換されてよい5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基より成る基から選ばれ;ここで、置換基R8と隣接する置換基R1は、1以上の基R9により置換されてよいモノあるいはポリ環式の脂肪族もしくは芳香族環構造を随意に形成してよく;
R9は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、Si(R10)3、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、1以上の基R10により置換されてよく、1以上の隣接しないCH2基は、Si(R10)2、C=NR10、P(=O)(R10)、SO、SO2、NR10、O、SもしくはCONR10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。)、または各場合に、1以上の基R10により置換されてよい6〜60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、または、1以上の基R10により置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または、各場合に1以上の基R10により置換されてよい5〜60個の芳香族もしくは複素環式芳香族環原子を有するアラルキルもしくはヘテロアラルキル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R9は、1以上の基R10により置換されてよいモノあるいはポリ環式の脂肪族環構造を随意に形成してよく;
R10は、H、D、F、1〜20個のC原子を有する脂肪族炭化水素基、または6〜30個のC原子を有する芳香族環構造より成る基から選ばれ、1以上のH原子は、DもしくはFで置き代えられてよく;ここで、2個以上の隣接する置換基R10は、たがいにモノもしくはポリ環式の脂肪族環構造を形成してよく;
iは、出現毎に、0、1または2であり;
mは、0、1または2であり;
n、o、p、q、rは、出現毎に同一であるか異なり、0、1、2、3または4であり;
s、t、uは、出現毎に同一であるか異なり、0、1または2であり;
ここで、s+o≦4、p+t≦4およびr+u≦4であり;
およびさらに、u+t+s≦2である。
第2の基は、水素原子が結合位置で結合して環を形成する。これは、以下のスキームにより示される:
Ar1、Ar2は、出現毎に同一であるか異なり、式(Ar−1)〜(Ar−33)の基およびその好ましい態様から選ばれる芳香族もしくは複素環式芳香族環構造であるか;
またはN-Ar1Ar2は、式(Ar1−1)〜(Ar1−19)の一つの基およびその好ましい態様であるか;
またはArs-NAr1Ar2は、式(Ar2−1)〜(Ar2−9)の一つの基およびその好ましい態様であり;
Eは、出現毎に同一であるか異なり、C(R7)2、O、SおよびNR7から選ばれ;
R1、R2、R3、R4、R5、R6、R8は、出現毎に同一であるか異なり、H、D、F、Si(R9)3、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、1以上の基R9により置換されてよく、1以上の隣接しないCH2基は、Oで置き代えられてよく、ここで、1以上のH原子は、DもしくはFで置き代えられてよい。)、または各場合に、1以上の基R9により置換されてよい6〜60個の芳香族環原子を有する芳香族環構造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〜R6もしくはR1とR8は、1以上の基R9により置換されてよいモノあるいはポリ環式の脂肪族環構造を随意に形成してよく;
R7は、出現毎に同一であるか異なり、H、D、F、Si(R9)3、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、1以上の基R9により置換されてよく、1以上の隣接しないCH2基は、Oで置き代えられてよく、ここで、1以上のH原子は、DもしくはFで置き代えられてよい。)、または各場合に、1以上の基R9により置換されてよい6〜60個の芳香族環原子を有する芳香族環構造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R7は、1以上の基R9により置換されてよいモノあるいはポリ環式の脂肪族環構造を随意に形成してよいか;
または(Ar1−1)、(Ar1−5)、(Ar1−9)、(Ar1−16)、(Ar1−17)、(Ar1−5a)、(Ar1−5b)、(Ar1−9a)、(Ar1−9b)、(Ar1−17a)、(Ar1−17b)、(Ar2−1)、(Ar3−8)、(Ar3−8a)および(Ar3−8b)中の炭素ブリッジに結合するR7は、出現毎に同一であるか異なり、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または、1以上の基R9により置換されてよい6〜30個のC原子を有する芳香族環構造より成る基から選ばれ;ここで、2個の基R7は、脂肪族もしくは芳香族であってよい環構造を互いに形成してもよいか;
または(Ar1−2)、(Ar1−6)、(Ar1−10)、(Ar1−19)、(Ar1−6a)、(Ar1−6b)、(Ar1−10a)、(Ar1−10b)、(Ar2−2)、(Ar3−9)および(Ar3−9a)中の窒素ブリッジに結合するR7は、出現毎に同一であるか異なり、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または、1以上の基R9により置換されてよい6〜30個のC原子を有する芳香族環構造より成る基から選ばれ;
R9は、出現毎に同一であるか異なり、H、D、F、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または6〜30個のC原子を有する芳香族環構造より成る基から選ばれ、夫々、1以上の基R10により置換されてよく、ここで、2個以上の隣接する置換基R9は、互いにモノあるいはポリ環式の脂肪族環構造を形成してよく;
R10は、H、D、F、1〜20個のC原子を有する脂肪族炭化水素基、または6〜30個のC原子を有する芳香族環構造より成る基から選ばれ、1以上のH原子は、DもしくはFで置き代えられてよく;ここで、2個以上の隣接する置換基R10は、モノもしくはポリ環式の脂肪族環構造をたがいに形成してよく;
iは、出現毎に、0,1または2であり;
mは、0または1、好ましくは、0であり;
o、p、rは、出現毎に同一であるか異なり、0、1または2、好ましくは、0であり;
n、qは、出現毎に同一であるか異なり、0、1または2、好ましくは、0または1であり;
s、t、uは、出現毎に同一であるか異なり、0または1であり;
ここで、u+t+s≦2である。
a)反応性脱離基により置換されたさらなる芳香族基へのカップリングに伴われる1級アミンへの、または
b)2級アミンへの、または
c)トリアリールアミン誘導体への
カップリングによる、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
重合をこれらの方法により実行することができる方法と次いでポリマーを反応媒体から分離し、精製することができる方法は、当業者に知られており、文献、たとえば、WO 2003/048225、WO 2004/037887およびWO 2004/037887に詳細に記載されている。
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から購入することができる(酢酸パラジウム(II)、トリ-o-トリルホスフィン、無機物、溶媒)。
化合物(0−1)の合成
化合物(1−1)の合成
化合物(2−1)の合成
化合物3−1の合成
化合物4−1の合成
本発明によるOLEDと先行技術によるOLEDとが、WO 04/058911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(層の厚さの変化、材料)に適合される。
青色一重項発光のOLEDでは、本発明による試料E1(6.6%)、E2(7.6%)、E3(8.5%)、E4(7.5%)、E5(7.5%)、E6(7.3%)、E7(7.1%)は、参照試料V1(6.2%)と比べて、10mA/cm2において、より高い量子効率を示す。50mA/cm2における寿命LT80はさらに、本発明による試料E1(390時間)、E2(370時間)、E3(380時間)、E4(305時間)、E5(220時間)、E6(300時間)、E7(440時間)の場合、参照試料V1(135時間)の場合よりも、非常に良好である。
緑色燐光参照試料V2が製造され、本発明による試料E8およびE9と比較した。参照試料V2は、19.8%の外部量子効率と、2mA/cm2の電流密度における135時間の寿命(LT80@20mA/cm2)を有する。比較により、本発明による試料E8(19.2%)とE9(19.3%)は、同等の量子効率と、310時間(E8)および270時間(E9)の非常に良好な寿命を有する。
Claims (10)
- 式(1)の化合物;
Arsは、出現毎に同一であるか異なり、各場合に、1以上の基R7により置換されてもよい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であり;
基Ar1とAr2は、出現毎に同一であるか異なり、式(Ar−1)〜(Ar−25)および(Ar−28)〜(Ar−33)の基から選ばれるか:
または
基-NAr1Ar2は、以下の式(Ar1−1)〜(Ar1−19)の一つの基であり;
R 7 、R 8 は、出現毎に同一であるか異なり、H、D、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、1以上の基R 9 により置換されてよい。)、または各場合に、1以上の基R 9 により置換されてよい6〜60個のC原子を有する芳香族環構造より成る基から選ばれ;
R9は、出現毎に同一であるか異なり、D、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、または各場合に、1以上の基R10により置換されてよい6〜30個のC原子を有する芳香族環構造より成る基から選ばれ;
R10は、D、F、1〜20個のC原子を有する脂肪族炭化水素基、または6〜30個のC原子を有する芳香族環構造より成る基から選ばれ、1以上のH原子は、DもしくはFで置き代えられてよく;ここで、2個以上の隣接する置換基R10は、たがいにモノもしくはポリ環式の脂肪族環構造を形成してよく;
iは、出現毎に、0、1または2であり;
mは、0、1または2であり;
n、o、p、q、rは、出現毎に同一であるか異なり、0、1、2、3または4であり;
s、t、uは、出現毎に同一であるか異なり、0、1または2であり;
ここで、s+o≦4、p+t≦4およびr+u≦4であり;
およびさらに、u+t+s≦2である。 - 以下である請求項1〜3何れか1項記載の化合物:
Arsは、出現毎に同一であるか異なり、芳香族もしくは複素環式芳香族環構造であり、ここで、i=1または2に対して、Arsは、式(Ar3−1)〜(Ar3−12)の基から選ばれ;
R 7 、R 8 は、出現毎に同一であるか異なり、H、D、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、1以上の基R 9 により置換されてよい。)、または各場合に、1以上の基R 9 により置換されてよい6〜60個のC原子を有する芳香族環構造より成る基から選ばれ;
または、R 7 が、(Ar1−1)、(Ar1−5)、(Ar1−9)、(Ar1−16)、(Ar1−17)、(Ar1−5a)、(Ar1−5b)、(Ar1−9a)、(Ar1−9b)、(Ar1−17a)、(Ar1−17b)、(Ar3−8)、(Ar3−8a)および(Ar3−8b)中の炭素ブリッジに結合する場合は、R7は、出現毎に同一であるか異なり、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または、1以上の基R9により置換されてよい6〜30個のC原子を有する芳香族環構造より成る基から選ばれるか;
R10は、D、F、1〜20個のC原子を有する脂肪族炭化水素基、または6〜30個のC原子を有する芳香族環構造より成る基から選ばれ、1以上のH原子は、DもしくはFで置き代えられてよく;ここで、2個以上の隣接する置換基R10は、たがいにモノもしくはポリ環式の脂肪族環構造を形成してよく;
iは、出現毎に、0,1または2であり;
mは、0または1であり;
o、p、rは、出現毎に同一であるか異なり、0、1または2であり;
n、qは、出現毎に同一であるか異なり、0、1または2であり;
s、t、uは、出現毎に同一であるか異なり、0または1であり;
ここで、u+t+s≦2である。 - 1-,3-もしくは4-位で反応性脱離基により置換されたジスピロ[フルオレン-9,9'-アントラセン-10',9"-フルオレン]誘導体の、
a)反応性脱離基により置換されたさらなる芳香族基へのカップリングに伴われる1級アミンへの、または
b)2級アミンへの、または
c)トリアリールアミン誘導体への
カップリングによる、請求項1〜4何れか1項記載の化合物の製造方法。 - 請求項1〜4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とを含む調合物。
- 請求項1〜4何れか1項記載の化合物または請求項6記載の調合物の、電子素子での使用。
- 請求項1〜4何れか1項記載の少なくとも一つの化合物または請求項6記載の少なくとも一つの調合物を含む電子素子。
- 有機集積回路(O-IC)、有機電界効果トランジスタ(O-FET)、有機薄膜トランジスタ(O-TFT)、有機発光トランジスタ(O-LET)、有機太陽電池(OSC)、有機光学検査器、有機光受容器、有機電場消光素子(O-FQD)、発光電子化学電池(LEC)、有機レーザーダイオード(O-laser)および有機エレクトロルミッセンス素子(OLED)から選ばれることを特徴とする、請求項8記載の電子素子。
- 請求項1〜4何れか1項記載の化合物または請求項6記載の少なくとも一つの調合物が、正孔輸送もしくは正孔注入層において正孔輸送材料として、または電子ブロック層として、または励起子ブロック層として、または蛍光発光層のためのエミッターとして、または発光層におけるマトリックス材料として使用されることを特徴とし、有機エレクトロルミッセンス素子(OLED)から選ばれる請求項9記載の電子素子。
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JP2017502007A (ja) | 2017-01-19 |
CN105814170A (zh) | 2016-07-27 |
EP3080229A1 (de) | 2016-10-19 |
TWI654280B (zh) | 2019-03-21 |
US20160308129A1 (en) | 2016-10-20 |
US10158083B2 (en) | 2018-12-18 |
WO2015086108A1 (de) | 2015-06-18 |
KR20160097298A (ko) | 2016-08-17 |
CN105814170B (zh) | 2019-11-05 |
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KR101993129B1 (ko) | 2019-06-26 |
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