CN109890787A - 用于电子器件的材料 - Google Patents
用于电子器件的材料 Download PDFInfo
- Publication number
- CN109890787A CN109890787A CN201780065207.9A CN201780065207A CN109890787A CN 109890787 A CN109890787 A CN 109890787A CN 201780065207 A CN201780065207 A CN 201780065207A CN 109890787 A CN109890787 A CN 109890787A
- Authority
- CN
- China
- Prior art keywords
- group
- ring system
- alkyl
- aromatics
- referred
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims description 70
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- -1 fluoranthene amine compounds Chemical class 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000010410 layer Substances 0.000 claims description 125
- 125000003118 aryl group Chemical group 0.000 claims description 78
- 125000004122 cyclic group Chemical group 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 230000005540 biological transmission Effects 0.000 claims description 27
- 125000000304 alkynyl group Chemical group 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 13
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000005401 electroluminescence Methods 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- 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 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 7
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 5
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 150000004826 dibenzofurans Chemical class 0.000 claims description 4
- 150000002390 heteroarenes Chemical class 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 abstract description 29
- 239000002585 base Substances 0.000 description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 26
- 150000001412 amines Chemical class 0.000 description 19
- 239000011159 matrix material Substances 0.000 description 16
- 239000004305 biphenyl Substances 0.000 description 14
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 14
- 235000010290 biphenyl Nutrition 0.000 description 13
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
- 150000002220 fluorenes Chemical class 0.000 description 12
- 230000004888 barrier function Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 230000027756 respiratory electron transport chain Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- 125000005605 benzo group Chemical group 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical class C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000758 substrate Substances 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
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000004986 diarylamino group Chemical group 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 125000005259 triarylamine group Chemical group 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L Cs2CO3 Substances [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 150000003851 azoles Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 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
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-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
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-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
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-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
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-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
- SOVOUXSYSVSVIE-UHFFFAOYSA-N 3-(4-chlorophenyl)-7,10-diphenylfluoranthene Chemical compound ClC1=CC=C(C=C1)C=1C=CC=2C3=C(C=CC(=C3C3=CC=CC=1C=23)C1=CC=CC=C1)C1=CC=CC=C1 SOVOUXSYSVSVIE-UHFFFAOYSA-N 0.000 description 2
- DJCJDRMDEKPVLT-UHFFFAOYSA-N 3-(4-chlorophenyl)fluoranthene Chemical compound C1=CC(Cl)=CC=C1C1=CC=C2C3=C1C=CC=C3C1=CC=CC=C12 DJCJDRMDEKPVLT-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000005108 alkenylthio group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 2
- 150000008365 aromatic ketones Chemical class 0.000 description 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 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
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000004913 cyclooctene Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000005266 diarylamine group Chemical group 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
- 230000000694 effects Effects 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- 230000003760 hair shine Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- SWGQKRKXZZPKJA-UHFFFAOYSA-N indeno[2,1-a]fluorene-1,2-diamine Chemical compound C1=CC=C2C=C3C4=CC5=C(N)C(N)=CC=C5C4=CC=C3C2=C1 SWGQKRKXZZPKJA-UHFFFAOYSA-N 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 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 2
- 239000012071 phase Substances 0.000 description 2
- 239000011295 pitch Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 150000003921 pyrrolotriazines Chemical class 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LHXDLQBQYFFVNW-OIBJUYFYSA-N (-)-Fenchone Chemical compound C1C[C@@]2(C)C(=O)C(C)(C)[C@@H]1C2 LHXDLQBQYFFVNW-OIBJUYFYSA-N 0.000 description 1
- 229930006729 (1R,4S)-fenchone Natural products 0.000 description 1
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical class C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- 150000004868 1,2,5-thiadiazoles Chemical class 0.000 description 1
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- WWRCMNKATXZARA-UHFFFAOYSA-N 1-Isopropyl-2-methylbenzene Chemical compound CC(C)C1=CC=CC=C1C WWRCMNKATXZARA-UHFFFAOYSA-N 0.000 description 1
- OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 description 1
- LBNXAWYDQUGHGX-UHFFFAOYSA-N 1-Phenylheptane Chemical compound CCCCCCCC1=CC=CC=C1 LBNXAWYDQUGHGX-UHFFFAOYSA-N 0.000 description 1
- HYLLZXPMJRMUHH-UHFFFAOYSA-N 1-[2-(2-methoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOC HYLLZXPMJRMUHH-UHFFFAOYSA-N 0.000 description 1
- SNAQINZKMQFYFV-UHFFFAOYSA-N 1-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOC SNAQINZKMQFYFV-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- RERATEUBWLKDFE-UHFFFAOYSA-N 1-methoxy-2-[2-(2-methoxypropoxy)propoxy]propane Chemical compound COCC(C)OCC(C)OCC(C)OC RERATEUBWLKDFE-UHFFFAOYSA-N 0.000 description 1
- JCHJBEZBHANKGA-UHFFFAOYSA-N 1-methoxy-3,5-dimethylbenzene Chemical class COC1=CC(C)=CC(C)=C1 JCHJBEZBHANKGA-UHFFFAOYSA-N 0.000 description 1
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 1
- CKJOUKWDAKSVKW-UHFFFAOYSA-N 11h-benzo[a]fluoren-1-amine Chemical compound C1=CC=C2CC3=C4C(N)=CC=CC4=CC=C3C2=C1 CKJOUKWDAKSVKW-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- MREIFUWKYMNYTK-UHFFFAOYSA-N 1H-pyrrole Chemical class C=1C=CNC=1.C=1C=CNC=1 MREIFUWKYMNYTK-UHFFFAOYSA-N 0.000 description 1
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- ZNOVTXRBGFNYRX-UHFFFAOYSA-N 2-[[4-[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 ZNOVTXRBGFNYRX-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 description 1
- UTDCGTAAWGJIOW-UHFFFAOYSA-N 2h-indeno[1,2-g][1]benzofuran Chemical compound C1=C2C=CC=CC2=C2C1=C1OCC=C1C=C2 UTDCGTAAWGJIOW-UHFFFAOYSA-N 0.000 description 1
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical class C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 description 1
- ALGIYXGLGIECNT-UHFFFAOYSA-N 3h-benzo[e]indole Chemical class C1=CC=C2C(C=CN3)=C3C=CC2=C1 ALGIYXGLGIECNT-UHFFFAOYSA-N 0.000 description 1
- 229940077398 4-methyl anisole Drugs 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- YTOINOFCLFDHCG-UHFFFAOYSA-N 8-(4-chlorophenyl)fluoranthene Chemical compound ClC1=CC=C(C=C1)C=1C=C2C3=CC=CC4=CC=CC(C2=CC=1)=C43 YTOINOFCLFDHCG-UHFFFAOYSA-N 0.000 description 1
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical class C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 description 1
- MSJMEQRRQOBTRB-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3NC12.N1C=CC=CC=C1 Chemical compound C1=CC=CC=2C3=CC=CC=C3NC12.N1C=CC=CC=C1 MSJMEQRRQOBTRB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000555268 Dendroides Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- LEUZQDVZEOKCCV-UHFFFAOYSA-N N=NC=NN.N=NC=NN.C(COCCOCCOCCO)O Chemical compound N=NC=NN.N=NC=NN.C(COCCOCCOCCO)O LEUZQDVZEOKCCV-UHFFFAOYSA-N 0.000 description 1
- 229910005855 NiOx Inorganic materials 0.000 description 1
- 241000592274 Polypodium vulgare Species 0.000 description 1
- 229910002842 PtOx Inorganic materials 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 229910019571 Re2O7 Inorganic materials 0.000 description 1
- 229910002785 ReO3 Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- UAGZMXMHGIRPIY-UHFFFAOYSA-N [O].N1CCC1 Chemical compound [O].N1CCC1 UAGZMXMHGIRPIY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- LHXDLQBQYFFVNW-UHFFFAOYSA-N alpha-fenchone Natural products C1CC2(C)C(=O)C(C)(C)C1C2 LHXDLQBQYFFVNW-UHFFFAOYSA-N 0.000 description 1
- 229940088601 alpha-terpineol Drugs 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- XHNHAMXHOIUOBN-UHFFFAOYSA-N c1ccccc1.c1ccc2c(c1)sc1ccccc21 Chemical compound c1ccccc1.c1ccc2c(c1)sc1ccccc21 XHNHAMXHOIUOBN-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- JWSFKSVILLRVML-UHFFFAOYSA-N ctk0i2811 Chemical class NP=N JWSFKSVILLRVML-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 150000007858 diazaphosphole derivatives Chemical class 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002178 europium compounds Chemical class 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000260 fractional sublimation Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002518 isoindoles Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 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
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IBXNCJKFFQIKKY-UHFFFAOYSA-N n-propylacetylene Natural products CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000005054 naphthyridines Chemical class 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group 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
- CDKDZKXSXLNROY-UHFFFAOYSA-N octylbenzene Chemical compound CCCCCCCCC1=CC=CC=C1 CDKDZKXSXLNROY-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 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
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 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
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 150000005053 phenanthridines Chemical class 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 150000003004 phosphinoxides Chemical class 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- OIZINMVCRAJMNL-UHFFFAOYSA-N piperazine 1,2-thiazole Chemical compound N1CCNCC1.S1N=CC=C1 OIZINMVCRAJMNL-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 150000003216 pyrazines Chemical class 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
- 150000003233 pyrroles Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- YSZJKUDBYALHQE-UHFFFAOYSA-N rhenium trioxide Chemical compound O=[Re](=O)=O YSZJKUDBYALHQE-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
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 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
- 238000000926 separation method Methods 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 238000007832 transition metal-catalyzed coupling reaction Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- 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
- 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
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/70—Nitro radicals
- C07D307/71—Nitro radicals attached in position 5
- C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
- C07D307/74—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals
- C07D307/76—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals having carbonic acyl radicals or their thio or nitrogen analogues directly attached to the hydrazino or hydrazono radical, e.g. semicarbazides
-
- 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
-
- 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
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/633—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
-
- 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
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/95—Spiro compounds containing "not free" spiro atoms
- C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
- C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-membered rings
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本申请涉及式(I)的荧蒽胺化合物。这些化合物适用于电子器件。本申请还涉及制备所述化合物的方法和包含所述化合物的电子器件。
Description
本申请涉及下面进一步定义的式(I)的荧蒽胺化合物。这些化合物适用于电子器件。本申请还涉及制备所述化合物的方法以及包含所述化合物的电子器件。
在本申请的上下文中的电子器件应理解为所谓的有机电子器件,其包含有机半导体材料作为功能材料。更特别地,这些意指OLED(有机电致发光器件)。术语OLED意指具有一个或多个包含有机化合物的层并且在施加电压时发光的电子器件。OLED的结构和功能的一般原理是本领域技术人员已知的。
在电子器件中,特别是OLED中,对改善性能数据,特别是寿命、效率和工作电压有很大的兴趣。在这些方面,尚未找到任何完全令人满意的解决方案。
发光层和具有传输空穴功能的层对电子器件的性能数据具有巨大影响。为了用于这些层中,仍然在寻找新材料,特别是具有传输空穴性能和传输电子性能的材料。特别感兴趣的是在一种化合物中合并空穴传输性能和电子传输性能的材料。这种材料称为双极型材料。此处优选的是,空穴传输性能位于化合物的一部分中,并且电子传输性能位于化合物的另一部分中。
在现有技术中,特别是已知三芳胺化合物作为电子器件的空穴传输材料。
然而,仍然需要适用于电子器件的替代化合物。
关于在电子器件中使用的性能数据,尤其是关于寿命和效率,还需要改进。
现已发现,特定的荧蒽胺化合物非常适合用于电子器件,特别是用于OLED,还更特别地用于其中作为磷光发光体的基质材料。
因此,本申请提供了式(I)的化合物
其中出现的变量如下:
A是C(R1)2或是
其中虚线表示与六元芳族环连接的键;
Z在每种情况下相同或不同,并且是CR2或N或C,其中在[L1]i基团与Z基团键合时的具体情况下,Z基团为C;
X在每种情况下相同或不同,并且是CR3或N或C,其中在[L2]k基团与X基团键合时的具体情况下,X基团为C;
L1、L2在每种情况下相同或不同,并且是具有6~24个芳族环原子并且可以被一个或多个R4基团取代的芳族环系,或具有5~24个芳族环原子并且可以被一个或多个R4基团取代的杂芳族环系;
Ar1是具有6~24个芳族环原子并且可以被一个或多个R5基团取代的芳族环系,或具有5~24个芳族环原子并且可以被一个或多个R5基团取代的杂芳族环系,其中Ar1不包含与式(I)的胺氮原子直接键合的任何含氮杂芳基基团,并且其中Ar1和与其键合的取代基不含任何咔唑基团;
R1、R2、R3、R4在每种情况下相同或不同且选自H、D、F、C(=O)R6、CN、Si(R6)3、P(=O)(R6)2、OR6、S(=O)R6、S(=O)2R6、具有1~20个碳原子的直链的烷基或烷氧基基团、具有3~20个碳原子的支链或环状的烷基或烷氧基基团、具有2~20个碳原子的烯基或炔基基团、具有6~40个芳族环原子的芳族环系和具有5~40个芳族环原子的杂芳族环系;其中两个或更多个R1或R2或R3或R4基团可以相互连接并且可以形成环;其中提及的烷基、烷氧基、烯基和炔基基团以及提及的芳族环系和杂芳族环系可各自被一个或多个R6基团取代;并且其中提及的烷基、烷氧基、烯基和炔基基团中的一个或多个CH2基团可以被-R6C=CR6-、-C≡C-、Si(R6)2、C=O、C=NR6、-C(=O)O-、-C(=O)NR6-、NR6、P(=O)(R6)、-O-、-S-、SO或SO2代替;
R5在每种情况下相同或不同且选自H、D、Si(R6)3、OR6、具有1~20个碳原子的直链的烷基或烷氧基基团、具有3~20个碳原子的支链或环状的烷基或烷氧基基团、具有2~20个碳原子的烯基或炔基基团、具有6~40个芳族环原子的芳族环系和具有5~40个芳族环原子的杂芳族环系;其中两个或更多个R5基团可以相互连接并且可以形成环;其中提及的烷基、烷氧基、烯基和炔基基团以及提及的芳族环系和杂芳族环系可各自被一个或多个R6基团取代;并且其中提及的烷基、烷氧基、烯基和炔基基团中的一个或多个CH2基团可以被R6C=CR6-、-C≡C-、Si(R6)2、NR6、O-或-S-代替;
R6在每种情况下相同或不同且选自H、D、F、C(=O)R7、CN、Si(R7)3、P(=O)(R7)2、OR7、S(=O)R7、S(=O)2R7、具有1~20个碳原子的直链的烷基或烷氧基基团、具有3~20个碳原子的支链或环状的烷基或烷氧基基团、具有2~20个碳原子的烯基或炔基基团、具有6~40个芳族环原子的芳族环系和具有5~40个芳族环原子的杂芳族环系;其中两个或更多个R6基团可以相互连接并且可以形成环;其中提及的烷基、烷氧基、烯基和炔基基团以及提及的芳族环系和杂芳族环系可各自被一个或多个R7基团取代;并且其中提及的烷基、烷氧基、烯基和炔基基团中的一个或多个CH2基团可以被R7C=CR7-、-C≡C-、Si(R7)2、C=O、C=NR7、-C(=O)O-、-C(=O)NR7-、NR7、P(=O)(R7)、-O-、-S-、SO或SO2代替;
R7在每种情况下相同或不同且选自H、D、F、CN、具有1~20个碳原子的烷基或烷氧基基团、具有2~20个碳原子的烯基或炔基基团、具有6~40个芳族环原子的芳族环系和具有5~40个芳族环原子的杂芳族环系;其中两个或更多个R7基团可以相互连接并且可以形成环;并且其中提及的烷基、烷氧基、烯基和炔基基团以及芳族环系和杂芳族环系可以被F或CN取代;
i为0、1、2或3;且
k为0、1、2或3。
经过式(I)中的如下荧蒽基团的键是指荧蒽基团可以在任何位置处与式(I)结构的其余部分键合:
经过式(I)中的如下单元中的六元环的键是指所讨论的单元可以在六元环中的任何位置处与式(I)结构的其余部分键合:
如果i=0,则芴基或螺二芴基直接键合到胺氮原子上。如果k=0,则荧蒽基基团直接键合到胺氮原子上。
在本发明上下文中的芳基基团含有6~40个芳族环原子,其中没有一个是杂原子。在本发明上下文中的芳基基团是指简单的芳族环即苯,或稠合芳族多环如萘、菲或蒽。在本申请上下文中的稠合芳族多环由两个或更多个彼此稠合的简单芳族环构成。环之间的稠合在此处意味着环彼此共享至少一个边。
本发明上下文中的杂芳基基团含有5~40个芳族环原子,其中至少一个是杂原子。杂芳基基团的杂原子优选选自N、O和S。本发明上下文中的杂芳基基团是指简单的杂芳族环如吡啶、嘧啶或噻吩,或稠合杂芳族多环如喹啉或咔唑。在本申请上下文中的稠合杂芳族多环由两个或更多个彼此稠合的简单杂芳族环构成。环之间的稠合意味着环彼此共享至少一个边。
各自可以被上述基团取代并且可以通过任何所需位置连接到芳族或杂芳族体系的芳基或杂芳基基团特别是指衍生自如下物质的基团:苯、萘、蒽、菲、芘、二氢芘、苝、联三苯叉、荧蒽、苯并蒽、苯并菲、并四苯、并五苯、苯并芘、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、唑、苯并唑、萘并唑、蒽并唑、菲并唑、异唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、吡嗪、吩嗪、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、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、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、中氮茚和苯并噻二唑。
本发明上下文中的芳族环系在环系中含有6~60个碳原子并且不包含任何杂原子作为芳族环原子。因此,本发明上下文中的芳族环系不含任何杂芳基基团。本发明上下文中的芳族环系是指以下体系,所述体系不一定仅含有芳基基团,而是其中多个芳基基团也可以通过单键或通过非芳族单元例如一个或多个任选取代的C、Si、N、O或S原子键合。在这种情况下,基于体系中除H以外的原子总数,非芳族单元优选包含小于10%的除H以外的原子。例如,在本发明的上下文中,诸如9,9'-螺二芴、9,9'-二芳基芴、三芳基胺、二芳基醚和二苯乙烯的体系也被认为是芳族环系,并且同样地,其中两个或更多个芳基基团例如通过直链或环状烷基、烯基或炔基基团或通过甲硅烷基基团连接的体系也是如此。此外,其中两个或更多个芳基通过单键彼此连接的体系,例如诸如联苯和三联苯的体系,也被认为是本发明的上下文中的芳族环系。
本发明上下文中的杂芳族环系包含5~40个芳族环原子,其中至少一个是杂原子。杂芳族环系的杂原子优选选自N、O和/或S。杂芳族环系对应于上述芳族环系的定义,但具有至少一个杂原子作为芳族环原子之一。以此方式,它不同于本申请的定义意义上的芳族环系,根据该定义,所述芳族环系不能含有任何杂原子作为芳族环原子。
具有6~40个芳族环原子的芳族环系或具有5~40个芳族环原子的杂芳族环系具体指衍生自如下基团的基团:上文在芳基基团和杂芳基基团下提及的基团以及联苯、三联苯、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、茚并芴、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、茚并咔唑或这些基团的组合。
在本发明的上下文中,其中个别氢原子或CH2基团也可以被以上基团定义中提及的基团取代的具有1~20个碳原子的直链烷基基团和具有3~20个碳原子的支链或环状烷基基团和具有2~40个碳原子的烯基或炔基基团优选是指甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、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、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基基团。
其中个别氢原子或CH2基团也可以被在以上基团定义中提及的基团代替的具有1~20个碳原子的烷氧基或硫代烷基基团优选是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、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、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、正戊硫基、仲戊硫基、正己硫基、环己硫基、正庚硫基、环庚硫基、正辛硫基、环辛硫基、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、环戊烯硫基、己烯硫基、环己烯硫基、庚烯硫基、环庚烯硫基、辛烯硫基、环辛烯硫基、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。
在本申请的上下文中,两个或更多个基团可以一起形成环的措辞特别是指两个基团通过化学键彼此连接。然而,另外上述措辞也是指,如果两个基团之一为氢,则第二个基团键合到与氢原子键合的位置处,形成环。
优选地,在式(I)中,荧蒽基团键合在3位或4位处,其中位置编号如下:
优选地,在式(I)中,芴基基团或螺二芴基基团在位置1位、3位和4位中的一个位置处键合,更优选在两个位置1位和4位中的一个位置处键合,最优选键合在位置4位处。利用在所讨论的优选位置的键,获得了改进的化合物性能数据,特别是在用作磷光发光体的基质材料的情况下获得了改进的化合物性能数据。芴基基团或螺二芴基基团上的位置编号如下:
优选的是,A为C(R1)2。
优选的是,每个芳族六元环中不超过两个Z基团为N;更优选地,每个芳族六元环中仅一个Z基团是N。
优选地,Z为CR2或C,其中当[L1]i基团与其键合时,Z基团在该具体情况下为C。
优选的是,荧蒽基中不超过两个X基团为N;更优选地,荧蒽基中仅一个X基团是N。最优选地,X是CR3或C,其中当X基团键合到[L2]k基团时,X基团在该具体情况下是C。
L1、L2优选在每种情况下相同或不同,并且选自衍生自如下物质的二价基团或这些基团中两个或更多个的组合:苯、联苯、三联苯、芴、螺二芴、茚并芴、咔唑、二苯并呋喃或二苯并噻吩,各自任选地被R4基团取代。L1、L2在每种情况下更优选相同或不同,并且选自以下任选被R4基团取代的基团:对苯亚基、间苯亚基或邻苯亚基、萘亚基、联苯亚基、二苯并呋喃亚基和二苯并硫代苯亚基。优选地,提及的基团不被R4基团取代。
L1、L2优选选自下式的基团:
其中虚线键表示与所述式的基团连接的键,并且所述基团可以在自由位置处被一个或多个R4基团取代,但优选在自由位置处未取代。
优选地,Ar1是具有6~24个芳族环原子并且可以被一个或多个R5基团取代的芳族环系,或具有5~24个芳族环原子并且可以被一个或多个R5基团取代的杂芳族环系,其中Ar1不包含任何含氮杂芳基基团。更优选地,Ar1选自下列任选被R5基团取代的基团:苯基、联苯基、支化三联苯基、未支化的三联苯基、支化四联苯基、未支化的四联苯基、芴基、二苯并呋喃基、二苯并噻吩基、芴基苯亚基、二苯并呋喃基苯亚基、二苯并噻吩基苯亚基、菲基和联三苯叉基。
最优选地,Ar1选自如下基团:
所述基团可以在所示的未取代位置处被R5基团取代,但优选在这些位置未取代,并且其通过虚线键与式(I)的其余部分键合。
R1在每种情况下优选相同或不同,并且选自F,Si(R6)3,具有1~20个碳原子的直链烷基基团,具有3~20个碳原子的支链或环状的烷基基团,具有6~24个芳族环原子的芳族环系和具有5~24个芳族环原子的杂芳族环系;其中提及的烷基基团、提及的芳族环系和提及的杂芳族环系可以各自被一个或多个R6基团取代;并且其中与同一碳原子键合的两个R1基团可以相互连接以形成环,产生螺碳原子。在这种情况下,结果优选为包含螺碳原子的环丙基、环丁基、环戊基、环己基或环庚基环。
R2、R3和R4在每种情况下优选相同或不同,并且选自H,D,F,CN,Si(R6)3,具有1~20个碳原子的直链烷基基团,具有3~20个碳原子的支链或环状烷基基团,具有6~24个芳族环原子的芳族环系和具有5~24个芳族环原子的杂芳族环系;其中提及的烷基基团、提及的芳族环系和提及的杂芳族环系可各自被一个或多个R6基团取代;并且其中提及的烷基基团中的一个或多个CH2基团可以被-C≡C-、-R6C=CR6-、Si(R6)2、C=O、C=NR6、-NR6-、-O-、-S-、-C(=O)O-或-C(=O)NR6-代替;更优选地,R2是H或具有6~24个芳族环原子并且可以被一个或多个R6基团取代的芳族环系,或具有5~24个芳族环原子并且可以被一个或多个R6基团取代的杂芳族环系,最优选H。更优选地,R3是H或具有6~24个芳族环原子并且可以被一个或多个R6基团取代的芳族环系,或具有5~24个芳族环原子并且可以被一个或多个R6基团取代的杂芳族环系,最优选H。
R5在每种情况下优选相同或不同且选自H,D,Si(R6)3,具有1~20个碳原子的直链烷基基团,具有3~20个碳原子的支链或环状烷基基团,具有6~24个芳族环原子的芳族环系和具有5~24个芳族环原子的杂芳族环系;其中提及的烷基基团、提及的芳族环系和提及的杂芳族环系可以各自被一个或多个R6基团取代,其中R5和与R5键合的取代基不含任何咔唑基团。更优选地,R5是H或具有6~24个芳族环原子并且可以被一个或多个R6基团取代的芳族环系,其中与R5键合的取代基不含任何咔唑基团;最优选地,R5是H。
R6在每种情况下优选相同或不同,并且H,D,F,CN,Si(R7)3,具有1~20个碳原子的直链烷基基团,具有3~20个碳原子的支链或环状的烷基基团,具有6~24个芳族环原子的芳族环系和具有5~24个芳族环原子的杂芳族环系;其中提及的烷基基团、提及的芳族环系和提及的杂芳族环系可以各自被一个或多个R7基团取代;并且其中提及的烷基基团中的一个或多个CH2基团可以被-C≡C-、-R7C=CR7-、Si(R7)2、C=O、C=NR7、-NR7-、-O-、-S-、-C(=O)O-或-C(=O)NR7-代替。
标记i优选为0或1,更优选0。
标记k优选为1。对于这种化合物,在电子器件中,特别是在OLED中使用时,还更特别地用作OLED中的磷光发光体的基质材料时,获得改进的性能数据。这些改进尤其涉及器件的效率、寿命和工作电压。
优选的化合物对应于下式(I-1)至(I-12)之一:
其中出现的符号如上所定义。优选地,上述变量的优选实施方案适用于所述式。尤其优选的是,如上所述,荧蒽基团键合在3位处。还特别优选的是如下情况:Z为CR2,和/或X为CR3或C,其中当氮原子或L2基团与所讨论的X键合时,在该具体情况下X为C;和/或根据上述优选实施方案来定义L2;和/或根据上述优选实施方案来定义Ar1。
在上述式中特别优选的是式(I-1)、(I-2)、(I-5)、(I-6)、(I-7)、(I-8)、(I-11)和(I-12),还更优选的是式(I-5)和(I-6),且最优选的是式(I-6)。
优选的式(I)化合物如下所示:
式(I)的化合物能够通过本领域技术人员已知的合成有机化学的常规方法制备。在化合物的制备中,特别使用过渡金属催化的偶联反应,例如Buchwald偶联反应和Suzuki偶联反应。
为了制备其中荧蒽基基团直接与氨基氮原子键合的式(Ⅰ)化合物,所遵循的程序优选按照下面的方法进行(方案1)。在这种情况下,同样可以使用螺二芴基基团,而不是芴基基团。
方案1
R=任选的有机基团
Y=反应性基团,优选Cl、Br或I。
此处芴基胺在Buchwald反应中与带有反应性基团的荧蒽基衍生物反应。这样得到式(I)的化合物。
为了制备其中荧蒽基基团通过芳族连接基与氨基氮键合的式(I)化合物,所遵循的程序优选按照如下两种方法之一来进行(方案2和3)。在这种情况下,同样可以使用螺二芴基基团,而不是芴基基团。
方案2
R=任选的有机基团
Y=反应性基团,优选Cl、Br或I
Ar=芳亚基或杂芳亚基基团。
此处带有反应性基团的荧蒽基衍生物在Suzuki反应中与带有另外的反应性基团的芳基基团反应。以此方式,制备芳基取代的荧蒽基基团。后者随后在Buchwald反应中与芴基胺反应,得到式(I)的化合物。
方案3
R=任选的有机基团
Y=反应性基团,优选Cl、Br或I
Ar=芳亚基或杂芳亚基基团。
根据方案3的变体,Suzuki偶联和Buchwald偶联步骤的顺序已经相对于方案2的变体进行了转换。在这种情况下,具有反应性基团的芳基基团首先在Buchwald偶联中键合到芴基胺上的胺。然后,在随后的反应中,将荧蒽基基团引入Suzuki偶联中。
因此,本发明还提供制备式(I)的化合物的方法,其特征在于在Buchwald偶联反应中使芴基胺与芳族或杂芳族化合物反应。
在本发明的一个优选实施方案中,提及的芳族或杂芳族化合物包含荧蒽基基团。在本发明可选的同样优选的一个实施方案中,提及的芳族或杂芳族化合物不包含任何荧蒽基基团。在这种情况下,优选在随后的Suzuki反应中引入荧蒽基基团。
上述化合物,特别是被反应性离去基团比如溴、碘、氯、硼酸或硼酸酯取代的化合物,可用作生产相应的低聚物、树枝状大分子或聚合物的单体。合适的反应离去基团例如为溴,碘,氯,硼酸,硼酸酯,胺,具有末端C-C双键或C-C三键的烯基或炔基基团,环氧乙烷,氧杂环丁烷,进入环加成比如1,3-双极环加成的基团比如二烯或叠氮化物,羧酸衍生物,醇和硅烷。
因此,本发明还提供含有一种或多种式(I)化合物的低聚物、聚合物或树枝状大分子,其中一个或多个与所述聚合物、低聚物或树枝状大分子连接的键可以位于式(I)中被R1、R2、R3、R4或R5取代的任何期望位置处。根据式(I)的化合物的连接,所述化合物是低聚物或聚合物的侧链的一部分或主链的一部分。本发明上下文中的低聚物是指由至少三个单体单元形成的化合物。本发明上下文中的聚合物是指由至少十个单体单元形成的化合物。本发明的聚合物、低聚物和树枝状大分子可以是共轭的、部分共轭的或非共轭的。本发明的低聚物或聚合物可以是线性、支化的或树枝状的。在具有线性连接的结构中,式(I)的单元可以彼此直接连接,或者它们可以经由二价基团,例如经由取代或未取代的烷亚基基团、经由杂原子或经由二价芳族或杂芳族基团彼此连接。在支化的和树枝状结构中,三个或更多个式(I)的单元可以例如经由三价或更高价基团,例如经由三价或更高价的芳族或杂芳族基团连接,以得到支化或树枝状低聚物或聚合物。
对于低聚物、树枝状大分子和聚合物中的式(I)的重复单元,如上所述的相同的优选方案适用于式(I)的化合物。
为制备所述低聚物或聚合物,使本发明的单体均聚或与另外的单体共聚。合适且优选的共聚单体选自:芴(例如根据EP 842208或WO 2000/22026)、螺二芴(例如根据EP707020、EP 894107或WO 2006/061181)、对苯亚基(例如根据WO 1992/18552)、咔唑(例如根据WO 2004/070772或WO 2004/113468)、噻吩(例如根据EP 1028136)、二氢菲(例如根据WO2005/014689或WO 2007/006383)、顺式和反式茚并芴(例如根据WO 2004/041901或WO2004/113412)、酮(例如根据WO 2005/040302)、菲(例如根据WO 2005/104264或WO 2007/017066)或多个这些单元。所述聚合物、低聚物和树枝状大分子通常还含有另外的单元,例如:发光(荧光或磷光)单元,例如乙烯基三芳基胺(例如根据WO 2007/068325)或磷光金属络合物(例如根据WO 2006/003000);和/或电荷传输单元,特别是基于三芳基胺的那些。
本发明的聚合物和低聚物通常通过一种或多种单体类型的聚合来制备,其中至少一种单体导致聚合物中式(I)的重复单元。合适的聚合反应是本领域技术人员已知的并且在文献中进行了描述。导致形成C-C和C-N键的特别合适且优选的聚合反应为Suzuki聚合、Yamamoto聚合、Stille聚合和Hartwig-Buchwald聚合。
为了从液相对本发明的化合物进行处理,例如通过旋涂或通过印刷方法处理,需要本发明化合物的制剂。这些制剂可以例如为溶液、分散液或乳液。为此,可以优选使用两种或更多种溶剂的混合物。合适并优选的溶剂例如为甲苯,苯甲醚,邻二甲苯、间二甲苯或对二甲苯,苯甲酸甲酯,均三甲苯,四氢化萘,藜芦醚,THF,甲基-THF,THP,氯苯,二烷,苯氧基甲苯,特别是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-吡咯烷酮,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,异丙基苯,环己醇,环己酮,环己基苯,十氢化萘,十二烷基苯,苯甲酸乙酯,茚满,苯甲酸甲酯,NMP,对甲基异丙基苯,苯乙醚,1,4-二异丙基苯,二苄醚,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,三乙二醇二甲醚,二乙二醇单丁基醚,三丙二醇二甲醚,四乙二醇二甲醚,2-异丙基萘,戊基苯,己基苯,庚基苯,辛基苯,1,1-双(3,4-二甲基苯基)乙烷,或这些溶剂的混合物。
因此,本发明进一步提供了一种制剂,特别是溶液、分散液或乳液,其包含至少一种式(I)的化合物和至少一种溶剂,优选有机溶剂。能够制备这种溶液的方式是本领域技术人员已知的,并且描述于例如WO 2002/072714、WO 2003/019694及其中引用的文献中。
本发明的化合物适用于电子器件,特别是有机电致发光器件(OLED)。根据取代,所述化合物用于不同的功能和层。
因此,本发明还提供式(I)的化合物在电子器件中的用途。该电子器件优选选自如下器件:有机集成电路(OIC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机发光晶体管(OLET)、有机太阳能电池(OSC)、有机光学检测器、有机光感受器、有机场猝熄器件(OFQD)、有机发光电化学电池(OLEC)、有机激光二极管(O-激光器),更优选有机电致发光器件(OLED)。
如上所述,本发明还提供了包含至少一种式(I)的化合物的电子器件。该电子器件优选地选自上述器件。
更优选的是包含阳极、阴极和至少一个发光层的有机电致发光器件(OLED),特征在于,至少一个有机层(其可以是发光层、空穴传输层或另一层)包含至少一种式(I)的化合物。
除了阴极、阳极和发光层之外,所述有机电致发光器件还可以包含另外的层。这些层例如在每种情况中选自一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、电子阻挡层、激子阻挡层、中间层、电荷产生层(IDMC 2003,Taiwan;Session21OLED(5),T.Matsumoto,T.Nakada,J.Endo,K.Mori,N.Kawamura,A.Yokoi,J.Kido,Multiphoton Organic EL Device Having Charge Generation Layer)和/或有机或无机p/n结。
包含式(I)的化合物的有机电致发光器件的层的顺序优选如下:
阳极-空穴注入层-空穴传输层-任选的另外的一个或多个空穴传输层-任选的电子阻挡层-发光层-任选的空穴阻挡层-电子传输层-电子注入层-阴极。另外可以在OLED中存在其它层。
本发明的有机电致发光器件可以含有两个或更多个发光层。更优选地,在这种情况下这些发光层在380nm~750nm之间总共具有多个发光峰值,从而总体上导致白色发光;换言之,将发荧光或发磷光的并发蓝色、绿色、黄色、橙色或红色光的多种发光化合物用于所述发光层中。特别优选三层体系,即具有三个发光层的体系,其中三个层呈现蓝色、绿色和橙色或红色发光(关于基本结构参见例如WO 2005/011013)。本发明的化合物此处优选存在于空穴传输层、空穴注入层、电子阻挡层、发光层、空穴阻挡层和/或电子传输层中,更优选作为基质材料存在于发光层中、存在于空穴阻挡层和/或电子传输层中。
根据本发明优选的是,式(I)的化合物用于包含一种或多种磷光发光化合物的电子器件中。在这种情况下,所述化合物可以存在于不同的层中,优选存在于空穴传输层、电子阻挡层、空穴注入层、发光层、空穴阻挡层和/或电子传输层中。更优选地,它与磷光发光化合物以组合的方式存在于发光层中。
术语“磷光发光化合物”通常包括其中通过自旋禁阻跃迁,比如来自激发三重态或具有更高自旋量子数的状态比如五重态的跃迁而实现发光的化合物。
合适的磷光发光化合物(=三重态发光体)特别是在合适激发时发光、优选在可见光区域发光,并且还包含至少一种原子序数大于20、优选大于38且小于84、更优选大于56且小于80的原子的化合物。作为磷光发光化合物,优选使用含有铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的化合物,特别是含有铱、铂或铜的化合物。在本发明的上下文中,所有发光的铱、铂或铜的络合物都被认为是磷光发光化合物。
上述发光化合物的实例能够在申请WO 00/70655、WO 01/41512、WO 02/02714、WO02/15645、EP 1191613、EP 1191612、EP 1191614、WO 05/033244、WO 05/019373和US 2005/0258742中找到。通常,根据现有技术的用于磷光OLED的和本领域技术人员在有机电致发光器件领域中已知的所有磷光络合物都是适合的。本领域技术人员也可以在不付出创造性劳动的条件下,将其它磷光络合物与式(I)的化合物组合用于有机电致发光器件中。下表列出了更多实例:
在本发明的一个优选实施方案中,式(I)的化合物作为基质材料与一种或多种发光化合物、优选磷光发光化合物组合用于发光层中。所述磷光发光化合物优选为红色磷光发光体。这是式(I)的化合物的最强烈优选的用途。
在这种情况下,发光层中基质材料的比例对于荧光发光层来说为50.0体积%~99.9体积%,优选80.0体积%~99.5体积%,更优选92.0体积%~99.5体积%,而对于磷光发光层来说为85.0体积%~97.0体积%。
相应地,发光化合物的比例对于荧光发光层来说为0.1体积%~50.0体积%,优选0.5体积%~20.0体积%,更优选0.5体积%~8.0体积%,而对于磷光发光层来说为3.0体积%~15.0体积%。
有机电致发光器件的发光层还可以包含含有多种基质材料(混合基质体系)和/或多种发光化合物的体系。同样在这种情况下,发光化合物通常是在体系中具有较小比例的那些化合物,且基质材料是在体系中具有较大比例的那些化合物。然而,在个别情况下,体系中单种基质材料的比例可小于单种发光化合物的比例。
优选的是式(I)的化合物用作混合基质体系的组分。混合基质体系优选包含两种或三种不同的基质材料,更优选两种不同的基质材料。优选地,在这种情况下,两种材料中的一种是具有空穴传输性能的材料,且另一种材料是具有电子传输性能的材料。式(I)的化合物优选是具有空穴传输性能的基质材料。然而,混合基质组分所需的电子传输和空穴传输的性能也可以主要或完全合并在单种混合基质组分中,在所述情况下,另外的混合基质组分实现其它功能。两种不同的基质材料可以1:50~1:1、优选1:20~1:1、更优选1:10~1:1且最优选1:4~1:1的比例存在。优选在磷光有机电致发光器件中使用混合基质体系。关于混合基质体系的更详细信息的一个来源是申请WO 2010/108579。
混合基质体系可以包含一种或多种发光化合物,优选一种或多种磷光发光化合物。通常,混合基质体系优选用于磷光有机电致发光器件中。
根据在混合基质体系中使用的发光化合物的类型,能够与本发明化合物组合用作混合基质体系的基质组分的特别合适的基质材料选自下面对于磷光发光化合物所明确的优选基质材料或对于荧光发光化合物的优选基质材料。
用于混合基质体系的优选的磷光发光化合物与进一步详述的通常优选的磷光发光体材料相同。
在本发明的一个优选实施方案中,式(I)的化合物用作空穴传输材料。在所述情况下,所述化合物优选存在于空穴传输层、电子阻挡层或空穴注入层中。
根据本申请的空穴传输层是在阳极与发光层之间具有空穴传输功能的层。
空穴注入层和电子阻挡层在本申请的上下文中被理解为空穴传输层的特定实施方案。在阳极与发光层之间有多个空穴传输层的情况下,空穴注入层是空穴传输层,其直接邻接阳极或仅通过阳极的单个涂层与其隔开。在阳极与发光层之间有多个空穴传输层的情况下,电子阻挡层是直接邻接阳极侧的发光层的所述空穴传输层。优选地,本发明的OLED在阳极与发光层之间包含两个、三个或四个空穴传输层,其中至少一个层优选含有式(I)的化合物,更优选确切地一个或两个层含有式(I)的化合物。
如果式(I)的化合物用作空穴传输层、空穴注入层或电子阻挡层中的空穴传输材料,则所述化合物能够作为纯材料即以100%的比例用于空穴传输层中,或者它能够与一种或多种其它化合物组合使用。在一个优选的实施方案中,包含式(I)的化合物的有机层然后另外含有一种或多种p型掺杂剂。根据本发明使用的p型掺杂剂优选是能够氧化混合物中的一种或多种其它化合物的那些有机电子受体化合物。
p型掺杂剂的特别优选的实施方案是在WO 2011/073149、EP 1968131、EP2276085、EP 2213662、EP 1722602、EP 2045848、DE 102007031220、US 8044390、US8057712、WO 2009/003455、WO 2010/094378、WO 2011/120709、US 2010/0096600、WO 2012/095143和DE 102012209523中公开的化合物。
特别优选的p型掺杂剂是如下物质:醌二甲烷化合物;氮杂茚并芴二酮;氮杂迫苯并萘;氮杂联三苯叉;I2;金属卤化物,优选过渡金属卤化物;金属氧化物,优选包含至少一种过渡金属或第3主族的金属的金属氧化物;和过渡金属络合物,优选Cu、Co、Ni、Pd和Pt与含有至少一个氧原子作为键合位点的配体的络合物。还优选过渡金属氧化物作为掺杂剂,优选铼、钼和钨的氧化物,更优选Re2O7、MoO3、WO3和ReO3。
所述p型掺杂剂优选基本上均匀地分散在p型掺杂的层中。这能够例如通过p型掺杂剂和空穴传输材料基质的共蒸发来实现。
优选的p型掺杂剂特别地为如下化合物:
在本发明另一个优选的实施方案中,式(I)的化合物与如在US 2007/0092755中所述的六氮杂联三苯叉衍生物组合用作空穴传输材料。此处的六氮杂联三苯叉衍生物尤其优选用于单独的层中。
在另一个优选的实施方案中,本发明的化合物用于电子传输侧的一个或多个层中,优选用于空穴阻挡层和/或电子传输层中。在用于电子传输层的情况下,优选它们与金属络合物、优选与羟基喹啉金属盐、更优选与羟基喹啉锂组合使用。
下面列出了电子器件中的不同功能材料的优选实施方案。
优选的荧光发光化合物选自芳基胺类。在本发明的上下文中,芳基胺或芳族胺被理解为是指包含三个直接键合到氮上的取代或未取代的芳族或杂芳族环系的化合物。优选地,这些芳族或杂芳族环系中至少一者为稠合的环系,其更优选具有至少14个芳族环原子。其优选实例是芳族蒽胺、芳族蒽二胺、芳族芘胺、芳族芘二胺、芳族胺或芳族二胺。芳族蒽胺是指其中一个二芳基氨基基团直接键合到蒽基基团、优选在9位上键合的化合物。芳族蒽二胺是指其中两个二芳基氨基基团直接键合到蒽基基团、优选在9,10位上键合的化合物。芳族的芘胺、芘二胺、胺和二胺以类似的方式定义,其中二芳基氨基基团优选键合在芘的1位或1,6位上。还优选的发光化合物是如下物质:茚并芴胺或茚并芴二胺,例如根据WO 2006/108497或WO 2006/122630的,苯并茚并芴胺或苯并茚并芴二胺,例如根据WO2008/006449的,和二苯并茚并芴胺或二苯并茚并芴二胺,例如根据WO 2007/140847的,以及在WO 2010/012328中公开的具有稠合芳基基团的茚并芴衍生物。同样优选地是公开在WO2012/048780和WO 2013/185871中的芘芳基胺。同样优选地是公开在WO 2014/037077中的苯并茚并芴胺、公开在WO 2014/106522中的苯并芴胺和公开在WO 2014/111269中和WO2017/036574中的扩展的苯并茚并芴、公开在WO 2017/028940和WO 2017/028941中的吩嗪以及公开在WO 2016/150544中的键合到呋喃单元或噻吩单元的芴衍生物。
优选用于荧光发光化合物的有用基质材料包括各类物质的材料。优选的基质材料选自如下类别的物质:低聚芳亚基(例如根据EP 676461的2,2',7,7'-四苯基螺二芴,或二萘基蒽),特别是含有稠合芳族基团的低聚芳亚基;低聚芳亚基乙烯亚基(例如,根据EP676461的DPVBi或螺-DPVBi);多足金属络合物(例如,根据WO 2004/081017的);空穴传导化合物(例如,根据WO 2004/058911的);电子传导化合物,特别是酮、氧化膦、亚砜等(例如,根据WO 2005/084081和WO 2005/084082的);阻转异构体(例如,根据WO 2006/048268的);硼酸衍生物(例如根据WO 2006/117052的);或苯并蒽(例如根据WO 2008/145239的)。尤其优选的基质材料选自如下类别:低聚芳亚基,其包含萘、蒽、苯并蒽和/或芘,或这些化合物的阻转异构体;低聚芳亚基乙烯亚基;酮;氧化膦和亚砜。非常特别优选的基质材料选自如下类别:低聚芳亚基,其包含蒽、苯并蒽、苯并菲和/或芘,或这些化合物的阻转异构体。在本发明上下文中的低聚芳亚基应被认为是指其中至少三个芳基或芳亚基基团彼此键合的化合物。还优选的是如下物质:公开在WO 2006/097208、WO 2006/131192、WO 2007/065550、WO2007/110129、WO 2007/065678、WO 2008/145239、WO 2009/100925、WO 2011/054442和EP1553154中的蒽衍生物;公开在EP 1749809、EP 1905754和US 2012/0187826中的芘化合物;公开在WO 2015/158409中的苯并蒽基蒽化合物;公开在WO 2017/025165中的茚并苯并呋喃化合物;和公开在WO 2017/036573中的菲基蒽化合物。
用于磷光发光化合物的优选基质材料是式(I)的化合物以及如下物质:芳族酮、芳族氧化膦或芳族亚砜或砜,例如根据WO 2004/013080、WO 2004/093207、WO 2006/005627或WO 2010/006680的;三芳基胺;咔唑衍生物,例如CBP(N,N-二咔唑基联苯)或公开在WO2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527或WO 2008/086851中的咔唑衍生物;吲哚并咔唑衍生物,例如根据WO 2007/063754或WO 2008/056746的;茚并咔唑衍生物,例如根据WO 2010/136109、WO 2011/000455或WO 2013/041176的;氮杂咔唑衍生物,例如根据EP 1617710、EP 1617711、EP 1731584、JP 2005/347160的;双极性基质材料,例如根据WO 2007/137725的;硅烷,例如根据WO 2005/111172的;氮杂硼杂环戊二烯或硼酸酯,例如根据WO 2006/117052的;三嗪衍生物,例如根据WO 2010/015306、WO 2007/063754或WO2008/056746的;锌络合物,例如根据EP 652273或WO 2009/062578的;二氮杂硅杂环戊二烯或四氮杂硅杂环戊二烯衍生物,例如根据WO 2010/054729的;二氮磷杂环戊二烯衍生物,例如根据WO 2010/054730的;桥接咔唑衍生物,例如根据US 2009/0136779、WO 2010/050778、WO 2011/042107、WO 2011/088877或WO 2012/143080的;联三苯叉衍生物,例如根据WO2012/048781的;或内酰胺,例如根据WO 2011/116865或WO 2011/137951的。
在本发明的电子器件的空穴注入或空穴传输层或电子阻挡层或电子传输层中可以使用的合适的电荷传输材料为式(I)的化合物以及例如公开在Y.Shirota等人,Chem.Rev.2007,107(4),953-1010中的化合物、或根据现有技术在这些层中使用的其它材料。
优选地,本发明的OLED包括两个或更多个不同的空穴传输层。此处式(I)的化合物可以用于一个或多个或所有空穴传输层中。在一个优选的实施方案中,式(I)的化合物确切地用于一个或确切地两个空穴传输层中,并且在存在的另外的空穴传输层中使用其它化合物,优选芳族胺化合物。与式(I)的化合物一起使用的、优选用于本发明的OLED的空穴传输层中的其它化合物特别地是茚并芴胺衍生物(例如根据WO 06/122630或WO 06/100896的)、EP 1661888中公开的胺衍生物、六氮杂联三苯叉衍生物(例如根据WO 01/049806的)、具有稠合芳族的胺衍生物(例如根据US 5,061,569的)、WO 95/09147中公开的胺衍生物、单苯并茚并芴胺(例如根据WO 08/006449的)、二苯并茚并芴胺(例如根据WO 07/140847的)、螺二芴胺(例如根据WO 2012/034627和WO 2013/120577的)、芴胺(例如根据WO 2004/015937,WO2014/015938、WO 2014/015935和WO 2015/082056的)、螺二苯并吡喃胺(例如根据WO 2013/083216的)、二氢吖啶衍生物(例如根据WO 2012/150001的)、螺二苯并呋喃和螺二苯并噻吩(例如根据WO 2015/022051、WO 2016/102048和WO 2016/131521的)、菲二芳基胺(例如根据WO 2015/131976的)、螺三苯并环庚三烯酚酮(例如根据WO 2016/087017的)、具有间苯二胺基团的螺二芴(例如根据WO2016/078738的)、螺双吖啶(例如根据WO2015/158411的)、呫吨二芳基胺(例如根据WO2014/072017的)和具有二芳基氨基基团的9,10-二氢蒽螺化合物(根据WO2015/086108的)。
用于电子传输层的材料是根据现有技术用作电子传输层中的电子传输材料的任意材料。特别合适的是铝络合物如Alq3、锆络合物如Zrq4、锂络合物如Liq、苯并咪唑衍生物、三嗪衍生物、嘧啶衍生物、吡啶衍生物、吡嗪衍生物、喹喔啉衍生物、喹啉衍生物、二唑衍生物、芳族酮、内酰胺、硼烷、二氮杂磷杂环戊二烯衍生物和氧化膦衍生物。另外合适的材料是如在JP 2000/053957、WO 2003/060956、WO 2004/028217、WO 2004/080975和WO 2010/072300中公开的上述化合物的衍生物。
所述电子器件的优选阴极是:具有低逸出功的金属;由各种金属如碱土金属、碱金属、主族金属或镧系元素(例如Ca、Ba、Mg、Al、In、Mg、Yb、Sm等)构成的金属合金或多层结构。此外合适的是由碱金属或碱土金属和银构成的合金,例如由镁和银构成的合金。在多层结构的情况中,除了所述金属之外,还可使用具有相对高逸出功的其它金属如Ag或Al,在该情况中通常使用所述金属的组合如例如Ca/Ag、Mg/Ag或Ba/Ag。还可以优选将具有高介电常数的材料的薄中间层引入金属阴极与有机半导体之间。用于此目的的有用材料的实例是碱金属氟化物或碱土金属氟化物,还有相应的氧化物或碳酸盐(例如LiF、Li2O、BaF2、MgO、NaF、CsF、Cs2CO3等)。此外,羟基喹啉锂(LiQ)也可以用于此目的。该层的层厚度优选为0.5~5nm。
优选的阳极是具有高逸出功的材料。优选地,阳极具有相对于真空大于4.5eV的逸出功。首先,具有高氧化还原电位的金属如例如Ag、Pt或Au适用于此目的。其次,金属/金属氧化物电极(例如Al/Ni/NiOx、Al/PtOx)也可以是优选的。对于一些应用,所述电极中的至少一个必须是透明的或部分透明的,以使得能够照射有机材料(有机太阳能电池)或发射光(OLED、O-激光器)。此处优选的阳极材料是导电混合金属氧化物。特别优选的是氧化铟锡(ITO)或氧化铟锌(IZO)。还优选导电的掺杂的有机材料,特别是导电的掺杂的聚合物。另外,阳极也可以由两个或更多个层构成,例如由ITO内层和金属氧化物外层构成,所述金属氧化物优选为氧化钨、氧化钼或氧化钒。
所述器件(根据应用)被适当地结构化,设置接触连接并最终密封,以排除水和空气的有害影响。
在一个优选实施方案中,电子器件的特征在于,利用升华法涂布一个或多个层。在这种情况下,材料在真空升华系统中在小于10-5毫巴、优选小于10-6毫巴的初始压力下通过气相沉积来施加。然而,在这种情况下,初始压力也可更低,例如小于10-7毫巴。
同样优选如下电子器件,所述电子器件的特征在于通过OVPD(有机气相沉积)方法或者借助于载气升华,涂布一个或多个层。在这种情况下,在10-5毫巴~1巴之间的压力下施加所述材料。该方法中的一个特别情况是OVJP(有机蒸气喷印)方法,其中通过喷嘴直接施加该材料,并因此结构化(例如M.S.Arnold等人,Appl.Phys.Lett.2008,92,053301)。
另外优选一种电子器件,所述电子器件的特征在于从溶液中产生一个或多个层,比如通过旋涂,或者通过任意印刷方法,比如丝网印刷、柔性版印刷、喷嘴印刷或胶版印刷,但更优选LITI(光引发热成像、热转印)或喷墨印刷。为了该目的,需要可溶的式(I)的化合物。通过适当取代化合物能够实现高溶解度。
还优选的是,通过从溶液施加一个层或多个层并通过升华法施加一个层或多个层来制造本发明的电子器件。
根据本发明,包含一种或多种式(I)的化合物的电子器件能够用于显示器中,作为光源用于照明应用中和作为光源用于医学和/或美容应用(例如光疗法)中。
实施例
A)合成例
除非另有说明,否则下面的合成是在保护气氛下在干燥的溶剂中进行。
a)联苯-4-基(9,9-二甲基-9H-芴-1-基)胺(1a)
首先将36g(212mmol,1.0当量)的4-氨基联苯与57.8g(177mmol,1.0当量)的1-溴二甲基芴和2.4g(212mmol,1.20当量)的叔戊醇钠[14593-46-5]一起加入600ml无水甲苯中并脱气30分钟。随后,添加398mg(1.77mmol,0.01当量)的乙酸钯(II)[3375-31-3]和1.46g(3.56mmol,0.02当量)的2-二环己基膦基-2’,6’-二甲氧基联苯SPHOS[657408-07-6]并将混合物在回流下加热过夜。反应结束后,将混合物冷却至室温并用500ml水萃取。随后,将水相用甲苯洗涤三次,将合并的有机相用硫酸钠干燥,并在旋转蒸发器上除去溶剂。将棕色残余物溶于约200ml甲苯中并通过硅胶过滤。为了进一步纯化,进行从甲苯/庚烷中的重结晶。
收率:59g(164mmol),理论值的79%。
以类似方式制备如下物质:
b)联苯-4-基(4-溴苯基)(9,9-二甲基-9H-芴-4-基)胺(1b)
在1l四口烧瓶中,首先加入51.3g(142mmol,1.00当量)的联苯-4-基(9,9-二甲基-9H-芴-4-基)胺以及另外的75.6g(426mmol,3.00当量)的1-溴-4-氟苯[460-00-4]和92.5g(284mmol,2.00当量)的碳酸铯[534-17-8],并添加500ml的二甲基乙酰胺。将反应混合物在150℃下搅拌3天。在反应结束后,将混合物冷却至室温,并通过硅藻土滤出固体。浓缩母液,并在过滤后,用热甲醇通过搅拌来提取沉淀的固体。
收率:43g(135mmol),理论值的95%。
以类似方式制备如下物质:
c)联苯-4-基(9,9-二甲基-9H-芴-1-基)(4-荧蒽-3-基苯基)胺(1)
将27g(110.0mmol)的荧蒽-3-硼酸、56g(110.0mmol)的联苯-4-基(4-溴苯基)(9,9-二甲基-9H-芴-1-基)胺和26g(210.0mmol)的碳酸钠悬浮在500ml乙二醇二胺醚和500ml水中。向该悬浮液中添加913mg(3.0mmol)的三邻甲苯基膦,然后添加112mg(0.5mmol)的乙酸钯(II),并将反应混合物加热回流16小时。冷却后,除去有机相,通过硅胶过滤,用200ml水洗涤三次,然后浓缩至干。将产物用甲苯/庚烷(1:2)在硅胶上经柱层析纯化,最后在高真空下(p=5×10-7毫巴)下升华(纯度99.9%)。收率为56g(88mmol),相当于理论值的80%。
以类似方式制备以下化合物:
d)3-(4-氯苯基)荧蒽(1d)
将30g(156mmol)的1-溴-4-氯苯、37g(150mmol)的荧蒽基-3-硼酸和36g(340mmol)的碳酸钠悬浮在1000ml的乙二醇二胺醚和280ml的水中。向该悬浮液中添加1.8g(1.5mmol)的四(三苯基膦)钯(0),并将反应混合物加热回流16小时。冷却后,分离有机相,通过硅胶过滤,用200ml水洗涤三次,然后浓缩至干。收率为30g(97mmol),相当于理论值的65%。
以类似方式制备以下化合物:
e)3-(4-氯苯基)-7,10-二苯基荧蒽(1e)
在500ml的四口烧瓶中,将25.4g(58.7mmol,1.0当量)的3-溴-7,10-二苯基荧蒽、9.17g(58.7mmol,1.0当量)的4-氯苯基硼酸(CAS 1679-18-1)和6.22g(58.7mmol,1.0当量)的碳酸钠溶于150ml甲苯、36ml乙醇和77ml水中。在用氮气流脱气30分钟后,添加678mg(0.587mmol,0.01当量)的四(三苯基膦)钯,并将混合物加热回流过夜。反应结束后,分离各相,水相用甲苯萃取三次,然后用水洗涤合并的有机相。有机相用硫酸钠干燥,并将溶液在旋转蒸发器上浓缩。将残余物引入250ml乙醇中,并抽滤出形成的固体。
收率为25.6g(55mmol),相当于理论值的94%。
以类似方式制备如下物质:
f)联苯-4-基(9,9-二甲基-9H-芴-4-基)(4-荧蒽-3-基苯基)胺(26)
将21.6g(60mmol)的8-(4-氯苯基)荧蒽、18.7g(60mmol)的联苯-4-基(9,9-二甲基-9H-芴-4-基)胺、7.7g(80mmol)的叔丁醇钠、1.4g(5mmol)的三环己胺、561mg(2.5mmol)的乙酸钯(II)和300ml均三甲苯的混合物加热回流24小时。冷却后,添加200ml水,将混合物再搅拌30分钟,分离有机相,并将有机相通过短硅藻土床过滤,然后减压除去溶剂。将残余物从DMF中重结晶五次,最后分级升华两次(p约10-6毫巴,T=360~390℃)。收率:27g(42mmol),理论值的71%:HPLC测定值为99.9%。
以类似的方式,获得以下化合物:
B)器件实施例
制备本发明的OLED E1~E10和比较例OLED V1~V3,并分析它们的性质(表1和2)。
OLED按如下制备:在涂布之前,用氧等离子体、随后用氩等离子体对涂布有厚度为50nm的结构化ITO(氧化铟锡)的玻璃板进行处理。这些经等离子体处理的玻璃板形成施加OLED的基底。
OLED基本上具有以下层结构:基底/空穴注入层(HIL)/空穴传输层(HTL)/电子阻挡层(EBL)/发光层(EML)/可选的空穴阻挡层(HBL)/电子传输层(ETL),最后是阴极。阴极由厚度为100nm的铝层形成。OLED的确切结构能够在表1中找到。制备OLED所需的材料示于表3中。
在真空室中通过热气相沉积施加所有材料。在这种情况下,发光层总是由至少一种基质材料(主体材料)和发光掺杂剂(发光体)组成,所述发光掺杂剂以特定体积比例通过共蒸发添加到所述基质材料。以诸如IC5:IC3:TEG2(55%:35%:10%)的形式给出的细节此处是指,材料IC5以55%的体积比存在于所述层中,IC3以35%的比例存在于所述层中且TEG2以10%的比例存在于所述层中。类似地,所述电子传输层也可由两种材料的混合物组成。
以标准方式表征所述OLED。为此,确定电致发光光谱,在假定朗伯发光特性下从电流-电压-亮度特性线(IUL特性线)计算作为亮度函数的电流效率(以cd/A计量)、功率效率(以lm/W计量)和外量子效率(EQE,以百分比计量),此外确定寿命。在1000cd/m2的亮度下确定所述电致发光光谱,并用其计算CIE 1931x和y颜色坐标。表2中的参数U1000是指对于1000cd/m2的亮度所需要的电压。最后,EQE1000是指在1000cd/m2的工作亮度下的外量子效率。寿命LD定义为在恒定电流的操作过程中亮度从起始亮度下降到特定比例L1所经历的时间。给出的数字L0;j0=a mA/cm2,L1=b%是指在a mA/cm2下的工作过程中亮度在时间LD之后下降到其起始值的b%。
将获得的关于OLED的数据列于表2中。
在实验E1~E5中,根据本申请的材料EG26、EG87、EG88、EG23和EG30用作发光层中红色磷光发光体的基质材料。OLED V1~V3与OLED E1~E5的区别仅在于用作发光层中的基质的材料(PA1、PA2和PA3)。在其它方面,它们具有相同的结构。发现本发明的OLED E1~E5都具有明显比比较例OLED V1~V3更长的寿命。
实验E6~E8表明本发明的化合物(EG18、EG71和EG85)作为空穴阻挡材料具有极好的适用性。
实验E9和E10表明本发明的化合物(EG3、EG37)作为电子传输材料具有极好的适用性。
Claims (19)
1.式(I)的化合物
其中出现的变量如下:
A是C(R1)2或是
其中虚线表示与六元芳族环连接的键;
Z在每种情况下相同或不同,并且是CR2或N或C,其中在[L1]i基团与Z基团键合时的具体情况下,所述Z基团为C;
X在每种情况下相同或不同,并且是CR3或N或C,其中在[L2]k基团与X基团键合时的具体情况下,所述X基团为C;
L1、L2在每种情况下相同或不同,并且是具有6~24个芳族环原子并且可以被一个或多个R4基团取代的芳族环系,或具有5~24个芳族环原子并且可以被一个或多个R4基团取代的杂芳族环系;
Ar1是具有6~24个芳族环原子并且可以被一个或多个R5基团取代的芳族环系,或具有5~24个芳族环原子并且可以被一个或多个R5基团取代的杂芳族环系,其中Ar1不包含与所述式(I)的胺氮原子直接键合的任何含氮杂芳基基团,并且其中Ar1和与其键合的取代基不含任何咔唑基团;
R1、R2、R3、R4在每种情况下相同或不同且选自H、D、F、C(=O)R6、CN、Si(R6)3、P(=O)(R6)2、OR6、S(=O)R6、S(=O)2R6、具有1~20个碳原子的直链的烷基或烷氧基基团、具有3~20个碳原子的支链或环状的烷基或烷氧基基团、具有2~20个碳原子的烯基或炔基基团、具有6~40个芳族环原子的芳族环系和具有5~40个芳族环原子的杂芳族环系;其中两个或更多个R1或R2或R3或R4基团可以相互连接并且可以形成环;其中提及的所述烷基、烷氧基、烯基和炔基基团以及提及的所述芳族环系和杂芳族环系可各自被一个或多个R6基团取代;并且其中提及的所述烷基、烷氧基、烯基和炔基基团中的一个或多个CH2基团可以被-R6C=CR6-、-C≡C-、Si(R6)2、C=O、C=NR6、-C(=O)O-、-C(=O)NR6-、NR6、P(=O)(R6)、-O-、-S-、SO或SO2代替;
R5在每种情况下相同或不同且选自H、D、Si(R6)3、OR6、具有1~20个碳原子的直链的烷基或烷氧基基团、具有3~20个碳原子的支链或环状的烷基或烷氧基基团、具有2~20个碳原子的烯基或炔基基团、具有6~40个芳族环原子的芳族环系和具有5~40个芳族环原子的杂芳族环系;其中两个或更多个R5基团可以相互连接并且可以形成环;其中提及的所述烷基、烷氧基、烯基和炔基基团以及提及的所述芳族环系和杂芳族环系可各自被一个或多个R6基团取代;并且其中提及的所述烷基、烷氧基、烯基和炔基基团中的一个或多个CH2基团可以被R6C=CR6-、-C≡C-、Si(R6)2、NR6、O-或-S-代替;
R6在每种情况下相同或不同且选自H、D、F、C(=O)R7、CN、Si(R7)3、P(=O)(R7)2、OR7、S(=O)R7、S(=O)2R7、具有1~20个碳原子的直链的烷基或烷氧基基团、具有3~20个碳原子的支链或环状的烷基或烷氧基基团、具有2~20个碳原子的烯基或炔基基团、具有6~40个芳族环原子的芳族环系和具有5~40个芳族环原子的杂芳族环系;其中两个或更多个R6基团可以相互连接并且可以形成环;其中提及的所述烷基、烷氧基、烯基和炔基基团以及提及的所述芳族环系和杂芳族环系可各自被一个或多个R7基团取代;并且其中提及的所述烷基、烷氧基、烯基和炔基基团中的一个或多个CH2基团可以被R7C=CR7-、-C≡C-、Si(R7)2、C=O、C=NR7、-C(=O)O-、-C(=O)NR7-、NR7、P(=O)(R7)、-O-、-S-、SO或SO2代替;
R7在每种情况下相同或不同且选自H、D、F、CN、具有1~20个碳原子的烷基或烷氧基基团、具有2~20个碳原子的烯基或炔基基团、具有6~40个芳族环原子的芳族环系和具有5~40个芳族环原子的杂芳族环系;其中两个或更多个R7基团可以相互连接并且可以形成环;并且其中提及的所述烷基、烷氧基、烯基和炔基基团以及提及的芳族环系和杂芳族环系可以被F或CN取代;
i为0、1、2或3;且
k为0、1、2或3。
2.根据权利要求1所述的化合物,其特征在于所述荧蒽基团键合在3位或4位,其中位置编号如下:
3.根据权利要求1或2所述的化合物,其特征在于式(I)中的式
的基团键合在1位、3位和4位中的一个位置处。
4.根据权利要求1~3中一项或多项所述的化合物,其特征在于L1、L2在每种情况下相同或不同,并且选自衍生自如下物质的二价基团或这些基团中两个或更多个的组合:苯、联苯、三联苯、芴、螺二芴、茚并芴、咔唑、二苯并呋喃或二苯并噻吩,各自任选地被R4基团取代。
5.根据权利要求1~4中一项或多项所述的化合物,其特征在于Ar1选自下列任选被R5基团取代的基团:苯基、联苯基、支化三联苯基、未支化的三联苯基、支化四联苯基、未支化的四联苯基、芴基、二苯并呋喃基、二苯并噻吩基、芴基苯亚基、二苯并呋喃基苯亚基、二苯并噻吩基苯亚基、菲基和联三苯叉基。
6.根据权利要求1~5中一项或多项所述的化合物,其特征在于R1在每种情况下相同或不同,并且选自F,Si(R6)3,具有1~20个碳原子的直链烷基基团,具有3~20个碳原子的支链或环状的烷基基团,具有6~24个芳族环原子的芳族环系和具有5~24个芳族环原子的杂芳族环系;其中提及的所述烷基基团、提及的所述芳族环系和提及的所述杂芳族环系可以各自被一个或多个R6基团取代;并且其中与同一碳原子键合的两个R1基团可以相互连接以形成环,产生螺碳原子。
7.根据权利要求1~6中一项或多项所述的化合物,其特征在于R2、R3和R4在每种情况下相同或不同,并且选自H、D、F、CN、Si(R6)3、具有1~20个碳原子的直链烷基基团、具有3~20个碳原子的支链或环状的烷基基团、具有6~24个芳族环原子的芳族环系和具有5~24个芳族环原子的杂芳族环系;其中提及的所述烷基基团、提及的所述芳族环系和提及的所述杂芳族环系可各自被一个或多个R6基团取代;并且其中提及的所述烷基基团中的一个或多个CH2基团可以被-C≡C-、-R6C=CR6-、Si(R6)2、C=O、C=NR6、-NR6-、-O-、-S-、-C(=O)O-或-C(=O)NR6-代替。
8.根据权利要求1~7中一项或多项所述的化合物,其特征在于R5在每种情况下相同或不同且选自H,D,Si(R6)3,具有1~20个碳原子的直链烷基基团,具有3~20个碳原子的支链或环状的烷基基团,具有6~24个芳族环原子的芳族环系和具有5~24个芳族环原子的杂芳族环系;其中提及的所述烷基基团、提及的所述芳族环系和提及的所述杂芳族环系可以各自被一个或多个R6基团取代,其中R5和与R5键合的取代基不含任何咔唑基团。
9.根据权利要求1~8中一项或多项所述的化合物,其特征在于R6在每种情况下相同或不同,并且选自H,D,F,CN,Si(R7)3,具有1~20个碳原子的直链烷基基团,具有3~20个碳原子的支链或环状的烷基基团,具有6~24个芳族环原子的芳族环系和具有5~24个芳族环原子的杂芳族环系;其中提及的所述烷基基团、提及的所述芳族环系和提及的所述杂芳族环系可以各自被一个或多个R7基团取代;并且其中提及的所述烷基基团中的一个或多个CH2基团可以被-C≡C-、-R7C=CR7-、Si(R7)2、C=O、C=NR7、-NR7-、-O-、-S-、-C(=O)O-或-C(=O)NR7-代替。
10.根据权利要求1~9中一项或多项所述的化合物,其特征在于i为0。
11.根据权利要求1~10中一项或多项所述的化合物,其特征在于k为1。
12.根据权利要求1~11中一项或多项所述的化合物,其特征在于所述化合物对应于式(I-1)~(I-12)中的一种,
其中出现的变量如权利要求1~11中的一项或多项所定义的。
13.一种用于制备根据权利要求1~12中一项或多项所述的式(I)化合物的方法,其特征在于在Buchwald偶联反应中使芴基胺与芳族或杂芳族化合物反应。
14.一种含有一种或多种根据权利要求1~12中一项或多项所述的式(I)化合物的低聚物、聚合物或树枝状大分子,其中一个或多个与所述聚合物、低聚物或树枝状大分子连接的键可以位于式(1)中被R1、R2、R3、R4或R5取代的任何期望位置处。
15.一种制剂,所述制剂包含至少一种根据权利要求1~12中一项或多项所述的化合物或根据权利要求14所述的聚合物、低聚物或树枝状大分子和至少一种溶剂。
16.一种电子器件,所述电子器件包含至少一种根据权利要求1~12中一项或多项所述的化合物或根据权利要求14所述的聚合物、低聚物或树枝状大分子。
17.根据权利要求16所述的电子器件,其特征在于所述电子器件是包含阳极、阴极和至少一个发光层的有机电致发光器件,其中所述至少一个发光层是所述器件的至少一个有机层,所述至少一个有机层可以是含有至少一种所述化合物的发光层或空穴传输层。
18.根据权利要求17所述的电子器件,其特征在于所述电子器件是包含阳极、阴极和至少一个发光层的有机电致发光器件,所述至少一个发光层包含发红光的磷光发光体,其中至少一种所述化合物作为基质材料存在于所述发光层中。
19.根据权利要求1~12中一项或多项所述的化合物用于电子器件中的用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP16196934 | 2016-11-02 | ||
EP16196934.0 | 2016-11-02 | ||
PCT/EP2017/077728 WO2018083053A1 (de) | 2016-11-02 | 2017-10-30 | Materialien für elektronische vorrichtungen |
Publications (1)
Publication Number | Publication Date |
---|---|
CN109890787A true CN109890787A (zh) | 2019-06-14 |
Family
ID=57240921
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201780065207.9A Pending CN109890787A (zh) | 2016-11-02 | 2017-10-30 | 用于电子器件的材料 |
Country Status (6)
Country | Link |
---|---|
US (1) | US11302870B2 (zh) |
EP (1) | EP3535240B1 (zh) |
JP (1) | JP2020512273A (zh) |
CN (1) | CN109890787A (zh) |
TW (1) | TWI745467B (zh) |
WO (1) | WO2018083053A1 (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021103317A1 (zh) * | 2019-11-26 | 2021-06-03 | 武汉华星光电半导体显示技术有限公司 | 以螺双吖啶为核的空穴传输材料及有机发光二极管 |
CN113717056A (zh) * | 2020-05-25 | 2021-11-30 | 广东阿格蕾雅光电材料有限公司 | 一种化合物及其应用 |
CN114401945A (zh) * | 2019-09-20 | 2022-04-26 | 默克专利有限公司 | 作为用于电子器件的材料的迫位缩合杂环化合物 |
WO2022100704A1 (zh) * | 2020-11-13 | 2022-05-19 | 阜阳欣奕华材料科技有限公司 | 化合物与有机电致发光器件、显示装置 |
WO2022140878A1 (zh) * | 2020-12-28 | 2022-07-07 | 京东方科技集团股份有限公司 | 有机电致发光器件和显示装置 |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102657649B1 (ko) * | 2014-07-21 | 2024-04-15 | 메르크 파텐트 게엠베하 | 전자 소자용 재료 |
KR102444279B1 (ko) * | 2019-03-05 | 2022-09-15 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
KR102041137B1 (ko) * | 2019-04-02 | 2019-11-07 | 머티어리얼사이언스 주식회사 | 유기 화합물 및 이를 포함하는 유기전계발광소자 |
WO2022243403A1 (de) | 2021-05-21 | 2022-11-24 | Merck Patent Gmbh | Verfahren zur kontinuierlichen aufreinigung von mindestens einem funktionalen material und vorrichtung zur kontinuierlichen aufreinigung von mindestens einem funktionalen material |
WO2023052377A1 (de) | 2021-09-30 | 2023-04-06 | Merck Patent Gmbh | Organische elektrolumineszierende vorrichtung |
KR20240072237A (ko) | 2021-09-30 | 2024-05-23 | 메르크 파텐트 게엠베하 | 유기 전계 발광 장치 |
WO2023061998A1 (de) | 2021-10-14 | 2023-04-20 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2023072976A1 (de) * | 2021-10-29 | 2023-05-04 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2023078812A1 (de) | 2021-11-02 | 2023-05-11 | Merck Patent Gmbh | Benzofuro[3,2-d]pyrimidin-2,4-dicarbonitril-derivate und ähnliche verbindungen für organische elektrolumineszenzvorrichtungen |
WO2023099430A1 (de) | 2021-12-02 | 2023-06-08 | Merck Patent Gmbh | Triphenylen-triazin-dibenzofuran/dibenzothiophen-derivate für organische elektrolumineszenzvorrichtungen |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0378757A (ja) * | 1989-08-23 | 1991-04-03 | Canon Inc | 電子写真感光体 |
KR101231124B1 (ko) * | 2009-12-29 | 2013-02-07 | 주식회사 알파켐 | 플루오란센 유도체 및 이를 이용한 유기전계발광소자 |
CN103524399A (zh) * | 2013-10-21 | 2014-01-22 | 北京绿人科技有限责任公司 | 一种有机化合物及其使用该有机化合物的电致发光器件 |
CN105669467A (zh) * | 2016-03-16 | 2016-06-15 | 上海道亦化工科技有限公司 | 一种基于荧蒽的化合物及其有机电致发光器件 |
Family Cites Families (159)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
DE4111878A1 (de) | 1991-04-11 | 1992-10-15 | Wacker Chemie Gmbh | Leiterpolymere mit konjugierten doppelbindungen |
EP0721935B1 (en) | 1993-09-29 | 2003-01-22 | Idemitsu Kosan Company Limited | Organic electroluminescent element and arylenediamine derivative |
JPH07133483A (ja) | 1993-11-09 | 1995-05-23 | Shinko Electric Ind Co Ltd | El素子用有機発光材料及びel素子 |
EP0676461B1 (de) | 1994-04-07 | 2002-08-14 | Covion Organic Semiconductors GmbH | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
DE4436773A1 (de) | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
JP3865406B2 (ja) | 1995-07-28 | 2007-01-10 | 住友化学株式会社 | 2,7−アリール−9−置換フルオレン及び9−置換フルオレンオリゴマー及びポリマー |
DE19614971A1 (de) | 1996-04-17 | 1997-10-23 | Hoechst Ag | Polymere mit Spiroatomen und ihre Verwendung als Elektrolumineszenzmaterialien |
JP3858951B2 (ja) | 1996-08-30 | 2006-12-20 | 三井化学株式会社 | 有機電界発光素子 |
JP3801326B2 (ja) | 1997-11-18 | 2006-07-26 | 三井化学株式会社 | 有機電界発光素子 |
JP3302945B2 (ja) | 1998-06-23 | 2002-07-15 | ネースディスプレイ・カンパニー・リミテッド | 新規な有機金属発光物質およびそれを含む有機電気発光素子 |
DE19846766A1 (de) | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere, enthaltend spezielle Fluorenbausteine mit verbesserten Eigenschaften |
US6166172A (en) | 1999-02-10 | 2000-12-26 | Carnegie Mellon University | Method of forming poly-(3-substituted) thiophenes |
KR100934420B1 (ko) | 1999-05-13 | 2009-12-29 | 더 트러스티즈 오브 프린스턴 유니버시티 | 전계인광에 기초한 고 효율의 유기 발광장치 |
AU1807201A (en) | 1999-12-01 | 2001-06-12 | Trustees Of Princeton University, The | Complexes of form L2MX as phosphorescent dopants for organic leds |
KR100377321B1 (ko) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
US6660410B2 (en) | 2000-03-27 | 2003-12-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
CN100505375C (zh) | 2000-08-11 | 2009-06-24 | 普林斯顿大学理事会 | 有机金属化合物和发射转换有机电致磷光 |
JP4154140B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物 |
JP4154139B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子 |
JP4154138B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子、表示装置及び金属配位化合物 |
JP4307839B2 (ja) | 2001-03-10 | 2009-08-05 | メルク パテント ゲーエムベーハー | 有機半導体の溶液および分散液 |
DE10141624A1 (de) | 2001-08-24 | 2003-03-06 | Covion Organic Semiconductors | Lösungen polymerer Halbleiter |
KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
ITRM20020411A1 (it) | 2002-08-01 | 2004-02-02 | Univ Roma La Sapienza | Derivati dello spirobifluorene, loro preparazione e loro uso. |
KR100924462B1 (ko) | 2002-08-23 | 2009-11-03 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자 및 안트라센 유도체 |
TWI276369B (en) | 2002-09-20 | 2007-03-11 | Idemitsu Kosan Co | Organic electroluminescent device |
GB0226010D0 (en) | 2002-11-08 | 2002-12-18 | Cambridge Display Tech Ltd | Polymers for use in organic electroluminescent devices |
CN100489056C (zh) | 2002-12-23 | 2009-05-20 | 默克专利有限公司 | 有机电致发光元件 |
DE10304819A1 (de) | 2003-02-06 | 2004-08-19 | Covion Organic Semiconductors Gmbh | Carbazol-enthaltende konjugierte Polymere und Blends, deren Darstellung und Verwendung |
DE10310887A1 (de) | 2003-03-11 | 2004-09-30 | Covion Organic Semiconductors Gmbh | Matallkomplexe |
KR101036391B1 (ko) | 2003-03-13 | 2011-05-23 | 이데미쓰 고산 가부시키가이샤 | 신규한 질소 함유 헤테로환 유도체 및 이를 이용한 유기 전기발광 소자 |
JP4411851B2 (ja) | 2003-03-19 | 2010-02-10 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
EP2281861A3 (de) | 2003-04-15 | 2012-03-28 | Merck Patent GmbH | Mischungen von organischen zur Emission befähigten Halbleitern und Matrixmaterialien, deren Verwendung und Elektronikbauteile enthaltend diese Mischungen |
EP1617711B1 (en) | 2003-04-23 | 2016-08-17 | Konica Minolta Holdings, Inc. | Organic electroluminescent device and display |
JP2004339064A (ja) | 2003-05-13 | 2004-12-02 | Mitsui Chemicals Inc | アミン化合物および該化合物を含有する有機電界発光素子 |
EP1491568A1 (en) | 2003-06-23 | 2004-12-29 | Covion Organic Semiconductors GmbH | Semiconductive Polymers |
DE10328627A1 (de) | 2003-06-26 | 2005-02-17 | Covion Organic Semiconductors Gmbh | Neue Materialien für die Elektrolumineszenz |
DE10333232A1 (de) | 2003-07-21 | 2007-10-11 | Merck Patent Gmbh | Organisches Elektrolumineszenzelement |
DE10337346A1 (de) | 2003-08-12 | 2005-03-31 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere enthaltend Dihydrophenanthren-Einheiten und deren Verwendung |
DE10338550A1 (de) | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
DE10345572A1 (de) | 2003-09-29 | 2005-05-19 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
US7795801B2 (en) | 2003-09-30 | 2010-09-14 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, illuminator, display and compound |
EP2366752B1 (de) | 2003-10-22 | 2016-07-20 | Merck Patent GmbH | Neue materialien für die elektrolumineszenz und deren verwendung |
JP2006096964A (ja) | 2003-11-07 | 2006-04-13 | Sony Corp | 有機発光材料および有機材料の製造方法 |
KR100773524B1 (ko) * | 2003-12-24 | 2007-11-07 | 삼성에스디아이 주식회사 | 이핵 유기 금속 착물 및 이를 이용한 유기 전계 발광 소자 |
DE102004008304A1 (de) | 2004-02-20 | 2005-09-08 | Covion Organic Semiconductors Gmbh | Organische elektronische Vorrichtungen |
EP1722602A1 (en) | 2004-03-05 | 2006-11-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device and organic electroluminescent display |
US7790890B2 (en) | 2004-03-31 | 2010-09-07 | Konica Minolta Holdings, Inc. | Organic electroluminescence element material, organic electroluminescence element, display device and illumination device |
KR100787425B1 (ko) | 2004-11-29 | 2007-12-26 | 삼성에스디아이 주식회사 | 페닐카바졸계 화합물 및 이를 이용한 유기 전계 발광 소자 |
DE102004020298A1 (de) | 2004-04-26 | 2005-11-10 | Covion Organic Semiconductors Gmbh | Elektrolumineszierende Polymere und deren Verwendung |
DE102004023277A1 (de) | 2004-05-11 | 2005-12-01 | Covion Organic Semiconductors Gmbh | Neue Materialmischungen für die Elektrolumineszenz |
US7598388B2 (en) | 2004-05-18 | 2009-10-06 | The University Of Southern California | Carbene containing metal complexes as OLEDs |
WO2005115950A1 (ja) | 2004-05-27 | 2005-12-08 | Idemitsu Kosan Co., Ltd. | 非対称ピレン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
JP4862248B2 (ja) | 2004-06-04 | 2012-01-25 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
DE102004032527A1 (de) | 2004-07-06 | 2006-02-02 | Covion Organic Semiconductors Gmbh | Elektrolumineszierende Polymere |
ITRM20040352A1 (it) | 2004-07-15 | 2004-10-15 | Univ Roma La Sapienza | Derivati oligomerici dello spirobifluorene, loro preparazione e loro uso. |
EP1655359A1 (de) | 2004-11-06 | 2006-05-10 | Covion Organic Semiconductors GmbH | Organische Elektrolumineszenzvorrichtung |
EP1669386A1 (de) | 2004-12-06 | 2006-06-14 | Covion Organic Semiconductors GmbH | Teilkonjugierte Polymere, deren Darstellung und Verwendung |
JP5242373B2 (ja) | 2005-03-16 | 2013-07-24 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネセンスデバイスのための新規材料 |
JP4358884B2 (ja) | 2005-03-18 | 2009-11-04 | 出光興産株式会社 | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
EP1869141B1 (de) | 2005-04-14 | 2020-03-11 | Merck Patent GmbH | Verbindungen für organische elektronische vorrichtungen |
KR101289923B1 (ko) | 2005-05-03 | 2013-07-25 | 메르크 파텐트 게엠베하 | 유기 전계발광 장치 및 그에 사용되는 붕산 및 보린산유도체 |
DE102005023437A1 (de) | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
DE102005026651A1 (de) | 2005-06-09 | 2006-12-14 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
JP2007015961A (ja) | 2005-07-06 | 2007-01-25 | Idemitsu Kosan Co Ltd | ピレン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子 |
BRPI0613785A2 (pt) | 2005-07-08 | 2011-02-01 | Unilever Nv | produto alimentìcio que contém amido, processo para a preparação de células vegetais intactas contendo amido e processo para a preparação do produto alimentìcio que contém amido |
DE102005037734B4 (de) | 2005-08-10 | 2018-02-08 | Merck Patent Gmbh | Elektrolumineszierende Polymere, ihre Verwendung und bifunktionelle monomere Verbindungen |
US20070092755A1 (en) | 2005-10-26 | 2007-04-26 | Eastman Kodak Company | Organic element for low voltage electroluminescent devices |
CN101321755B (zh) | 2005-12-01 | 2012-04-18 | 新日铁化学株式会社 | 有机电致发光元件用化合物及有机电致发光元件 |
DE102005058557A1 (de) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
WO2007065550A1 (de) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Neue materialien für organische elektrolumineszenzvorrichtungen |
DE102005060473A1 (de) | 2005-12-17 | 2007-06-28 | Merck Patent Gmbh | Konjugierte Polymere, deren Darstellung und Verwendung |
EP1968131A4 (en) | 2005-12-27 | 2009-08-19 | Idemitsu Kosan Co | ORGANIC ELECTROLUMINESCENT DEVICE AND MATERIAL THEREFOR |
DE102006013802A1 (de) | 2006-03-24 | 2007-09-27 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006025777A1 (de) | 2006-05-31 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006025846A1 (de) | 2006-06-02 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006031990A1 (de) | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
CN101511834B (zh) | 2006-11-09 | 2013-03-27 | 新日铁化学株式会社 | 有机场致发光元件用化合物及有机场致发光元件 |
DE102007002714A1 (de) | 2007-01-18 | 2008-07-31 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US8044390B2 (en) | 2007-05-25 | 2011-10-25 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent device, organic electroluminescent device, and organic electroluminescent display |
DE102007024850A1 (de) | 2007-05-29 | 2008-12-04 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102007031220B4 (de) | 2007-07-04 | 2022-04-28 | Novaled Gmbh | Chinoide Verbindungen und deren Verwendung in halbleitenden Matrixmaterialien, elektronischen und optoelektronischen Bauelementen |
US8288013B2 (en) | 2007-07-18 | 2012-10-16 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device |
DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
US7862908B2 (en) | 2007-11-26 | 2011-01-04 | National Tsing Hua University | Conjugated compounds containing hydroindoloacridine structural elements, and their use |
ATE554073T1 (de) | 2007-11-30 | 2012-05-15 | Idemitsu Kosan Co | Azaindenofluorendionderivat, material für ein organisches elektrolumineszierendes gerät und organisches lumineszierendes gerät |
DE102008008953B4 (de) | 2008-02-13 | 2019-05-09 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
TWI478624B (zh) | 2008-03-27 | 2015-03-21 | Nippon Steel & Sumikin Chem Co | Organic electroluminescent elements |
US8057712B2 (en) | 2008-04-29 | 2011-11-15 | Novaled Ag | Radialene compounds and their use |
DE102008033943A1 (de) | 2008-07-18 | 2010-01-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008035413A1 (de) | 2008-07-29 | 2010-02-04 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
DE102008036982A1 (de) | 2008-08-08 | 2010-02-11 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
JP2010093181A (ja) | 2008-10-10 | 2010-04-22 | Canon Inc | 有機発光素子 |
KR20100041043A (ko) | 2008-10-13 | 2010-04-22 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고 있는 유기 발광 소자 |
US8119037B2 (en) | 2008-10-16 | 2012-02-21 | Novaled Ag | Square planar transition metal complexes and organic semiconductive materials using them as well as electronic or optoelectric components |
KR20100048210A (ko) * | 2008-10-30 | 2010-05-11 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자 |
KR101506919B1 (ko) | 2008-10-31 | 2015-03-30 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전자 소자 |
DE102008056688A1 (de) | 2008-11-11 | 2010-05-12 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
KR20110097612A (ko) | 2008-11-11 | 2011-08-31 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자 |
DE102008064200A1 (de) | 2008-12-22 | 2010-07-01 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102009009277B4 (de) | 2009-02-17 | 2023-12-07 | Merck Patent Gmbh | Organische elektronische Vorrichtung, Verfahren zu deren Herstellung und Verwendung von Verbindungen |
DE102009014513A1 (de) | 2009-03-23 | 2010-09-30 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102009023155A1 (de) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009031021A1 (de) | 2009-06-30 | 2011-01-05 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009048791A1 (de) | 2009-10-08 | 2011-04-14 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009053191A1 (de) | 2009-11-06 | 2011-05-12 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
EP2513125B1 (de) | 2009-12-14 | 2014-10-29 | Basf Se | Metallkomplexe, enthaltend diazabenzimidazolcarben-liganden und deren verwendung in oleds |
US9353027B2 (en) | 2009-12-21 | 2016-05-31 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element using pyrene derivative |
DE102010005697A1 (de) | 2010-01-25 | 2011-07-28 | Merck Patent GmbH, 64293 | Verbindungen für elektronische Vorrichtungen |
DE102010012738A1 (de) | 2010-03-25 | 2011-09-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010013495A1 (de) | 2010-03-31 | 2011-10-06 | Siemens Aktiengesellschaft | Dotierstoff für eine Lochleiterschicht für organische Halbleiterbauelemente und Verwendung dazu |
DE102010019306B4 (de) | 2010-05-04 | 2021-05-20 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
DE102010045405A1 (de) | 2010-09-15 | 2012-03-15 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
CN102082232A (zh) | 2010-09-16 | 2011-06-01 | 昆山维信诺显示技术有限公司 | 一种蓝光有机电致发光器件 |
DE102010048608A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010048607A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
JP6022478B2 (ja) | 2011-01-13 | 2016-11-09 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
EP2699571B1 (de) | 2011-04-18 | 2018-09-05 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
KR101884496B1 (ko) | 2011-05-05 | 2018-08-01 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
EP2758372B1 (de) | 2011-09-21 | 2017-05-17 | Merck Patent GmbH | Carbazolderivate für organische elektrolumineszenzvorrichtungen |
US10305040B2 (en) | 2011-11-17 | 2019-05-28 | Merck Patent Gmbh | Spiro dihydroacridine derivatives and the use thereof as materials for organic electroluminescence devices |
KR101290015B1 (ko) | 2011-11-30 | 2013-07-30 | 주식회사 두산 | 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자 |
WO2013120577A1 (en) | 2012-02-14 | 2013-08-22 | Merck Patent Gmbh | Spirobifluorene compounds for organic electroluminescent devices |
DE102012209523A1 (de) | 2012-06-06 | 2013-12-12 | Osram Opto Semiconductors Gmbh | Hauptgruppenmetallkomplexe als p-Dotanden für organische elektronische Matrixmaterialien |
DE112013002910T5 (de) | 2012-06-12 | 2015-03-19 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
JP6422861B2 (ja) * | 2012-06-29 | 2018-11-14 | メルク パテント ゲーエムベーハー | 2,7−ピレン構造単位を含むポリマー |
CN108054293B (zh) | 2012-07-23 | 2020-05-22 | 默克专利有限公司 | 2-二芳基氨基芴的衍生物和含有所述2-二芳基氨基芴衍生物的有机电子复合体 |
EP2875092B1 (de) | 2012-07-23 | 2017-02-15 | Merck Patent GmbH | Verbindungen und organische elektrolumineszierende vorrichtungen |
KR102268222B1 (ko) | 2012-07-23 | 2021-06-22 | 메르크 파텐트 게엠베하 | 플루오렌 및 이를 함유하는 전자 소자 |
US10439145B2 (en) | 2012-09-04 | 2019-10-08 | Merck Patent Gmbh | Compounds for electronic devices |
EP2907803B1 (en) | 2012-10-12 | 2021-08-18 | Toray Industries, Inc. | Fluoranthene derivative, luminescent element material containing same, and luminescent element |
CN104781247B (zh) | 2012-11-12 | 2017-08-15 | 默克专利有限公司 | 用于电子器件的材料 |
US20150329772A1 (en) | 2013-01-03 | 2015-11-19 | Merck Patent Gmbh | Materials for Electronic Devices |
KR102005387B1 (ko) | 2013-06-05 | 2019-07-30 | 덕산네오룩스 주식회사 | 광효율 개선층을 포함하는 유기전기소자 및 이를 포함하는 전자 장치 |
KR102066437B1 (ko) | 2013-07-02 | 2020-01-15 | 덕산네오룩스 주식회사 | 광효율 개선층을 포함하는 유기전기소자 및 이를 포함하는 전자 장치 |
KR102137429B1 (ko) | 2013-07-11 | 2020-07-24 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치 |
US9978950B2 (en) | 2013-08-15 | 2018-05-22 | Merck Patent Gmbh | Materials for electronic devices |
KR102072756B1 (ko) | 2013-09-17 | 2020-02-03 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치 |
WO2014111269A2 (de) | 2013-10-14 | 2014-07-24 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR20240005971A (ko) | 2013-12-06 | 2024-01-12 | 메르크 파텐트 게엠베하 | 화합물 및 유기 전자 소자 |
KR101993129B1 (ko) | 2013-12-12 | 2019-06-26 | 메르크 파텐트 게엠베하 | 전자 소자용 물질 |
EP3114102B1 (de) | 2014-03-07 | 2017-12-06 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
CN106164074B (zh) | 2014-04-14 | 2019-01-18 | 默克专利有限公司 | 用于电子器件的材料 |
WO2015158409A1 (de) | 2014-04-16 | 2015-10-22 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR102357467B1 (ko) | 2014-07-22 | 2022-02-04 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 소자 |
EP3221292B1 (en) | 2014-11-18 | 2019-10-02 | Merck Patent GmbH | Materials for organic electroluminescent devices |
JP6776238B2 (ja) | 2014-12-01 | 2020-10-28 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
CN107112439B (zh) | 2014-12-22 | 2020-04-10 | 默克专利有限公司 | 用于电子器件的材料 |
CN118126004A (zh) | 2015-02-16 | 2024-06-04 | 默克专利有限公司 | 用于电子器件的基于螺二芴衍生物的材料 |
EP3274419B1 (en) | 2015-03-25 | 2019-04-03 | Merck Patent GmbH | Materials for organic electroluminescent devices |
KR102607963B1 (ko) | 2015-08-12 | 2023-11-29 | 메르크 파텐트 게엠베하 | 전자 소자용 물질 |
EP3334731B1 (en) | 2015-08-14 | 2021-03-03 | Merck Patent GmbH | Phenoxazine derivatives for organic electroluminescent devices |
KR102587272B1 (ko) | 2015-08-14 | 2023-10-10 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 페녹사진 유도체 |
EP3341448B1 (en) | 2015-08-28 | 2020-02-12 | Merck Patent GmbH | Compounds for electronic devices |
CN107848911B (zh) | 2015-08-28 | 2021-08-31 | 默克专利有限公司 | 6,9,15,18-四氢-对称引达省并[1,2-b:5,6-b’]二芴衍生物及其在电子器件中的用途 |
CN105175313B (zh) | 2015-09-02 | 2018-04-13 | 上海道亦化工科技有限公司 | 一种空穴注入化合物及其有机电致发光器件 |
CN107056626B (zh) | 2017-03-17 | 2019-03-22 | 吉林奥来德光电材料股份有限公司 | 一种化合物及其制备方法和应用 |
-
2017
- 2017-10-30 CN CN201780065207.9A patent/CN109890787A/zh active Pending
- 2017-10-30 EP EP17788266.9A patent/EP3535240B1/de active Active
- 2017-10-30 TW TW106137329A patent/TWI745467B/zh active
- 2017-10-30 WO PCT/EP2017/077728 patent/WO2018083053A1/de unknown
- 2017-10-30 US US16/346,598 patent/US11302870B2/en active Active
- 2017-10-30 JP JP2019522411A patent/JP2020512273A/ja not_active Withdrawn
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0378757A (ja) * | 1989-08-23 | 1991-04-03 | Canon Inc | 電子写真感光体 |
KR101231124B1 (ko) * | 2009-12-29 | 2013-02-07 | 주식회사 알파켐 | 플루오란센 유도체 및 이를 이용한 유기전계발광소자 |
CN103524399A (zh) * | 2013-10-21 | 2014-01-22 | 北京绿人科技有限责任公司 | 一种有机化合物及其使用该有机化合物的电致发光器件 |
CN105669467A (zh) * | 2016-03-16 | 2016-06-15 | 上海道亦化工科技有限公司 | 一种基于荧蒽的化合物及其有机电致发光器件 |
Non-Patent Citations (1)
Title |
---|
ACS: "无", 《STN REGISTRY》 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114401945A (zh) * | 2019-09-20 | 2022-04-26 | 默克专利有限公司 | 作为用于电子器件的材料的迫位缩合杂环化合物 |
WO2021103317A1 (zh) * | 2019-11-26 | 2021-06-03 | 武汉华星光电半导体显示技术有限公司 | 以螺双吖啶为核的空穴传输材料及有机发光二极管 |
CN113717056A (zh) * | 2020-05-25 | 2021-11-30 | 广东阿格蕾雅光电材料有限公司 | 一种化合物及其应用 |
WO2021238622A1 (zh) * | 2020-05-25 | 2021-12-02 | 广东阿格蕾雅光电材料有限公司 | 一种化合物及其应用 |
CN113717056B (zh) * | 2020-05-25 | 2022-09-16 | 广东阿格蕾雅光电材料有限公司 | 一种化合物及其应用 |
WO2022100704A1 (zh) * | 2020-11-13 | 2022-05-19 | 阜阳欣奕华材料科技有限公司 | 化合物与有机电致发光器件、显示装置 |
WO2022140878A1 (zh) * | 2020-12-28 | 2022-07-07 | 京东方科技集团股份有限公司 | 有机电致发光器件和显示装置 |
CN115088089A (zh) * | 2020-12-28 | 2022-09-20 | 京东方科技集团股份有限公司 | 有机电致发光器件和显示装置 |
CN115088089B (zh) * | 2020-12-28 | 2023-09-29 | 京东方科技集团股份有限公司 | 有机电致发光器件和显示装置 |
Also Published As
Publication number | Publication date |
---|---|
WO2018083053A1 (de) | 2018-05-11 |
JP2020512273A (ja) | 2020-04-23 |
US20190288206A1 (en) | 2019-09-19 |
EP3535240A1 (de) | 2019-09-11 |
KR20190079646A (ko) | 2019-07-05 |
US11302870B2 (en) | 2022-04-12 |
TWI745467B (zh) | 2021-11-11 |
TW201829369A (zh) | 2018-08-16 |
EP3535240B1 (de) | 2022-11-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN109890787A (zh) | 用于电子器件的材料 | |
CN106132910B (zh) | 电子器件的材料 | |
CN106164074B (zh) | 用于电子器件的材料 | |
CN104781247B (zh) | 用于电子器件的材料 | |
CN104884572B (zh) | 用于电子器件的材料 | |
CN105980518B (zh) | 化合物和有机电子器件 | |
CN105636944B (zh) | 用于电子器件的材料 | |
CN105492574B (zh) | 用于电子器件的材料 | |
CN104487541B (zh) | 化合物以及有机电致发光器件 | |
CN105814170B (zh) | 电子器件的材料 | |
CN104684886B (zh) | 用于电子器件的化合物 | |
CN104364245B (zh) | 用于有机电子器件的菲化合物 | |
CN103503187B (zh) | 用于电子器件的化合物 | |
CN107848911A (zh) | 6,9,15,18‑四氢‑对称引达省并[1,2‑b:5,6‑b’]二芴衍生物及其在电子器件中的用途 | |
CN107849444A (zh) | 用于电子器件的化合物 | |
CN107925007A (zh) | 用于电子器件的材料 | |
CN105593213B (zh) | 作为用于电子器件的材料的三芳基胺取代的苯并[h]喹啉-衍生物 | |
CN109791979A (zh) | 电子器件 | |
CN108699438A (zh) | 用于有机电致发光器件的材料 | |
CN107922402A (zh) | 用于有机电致发光器件的吩噁嗪衍生物 | |
CN108884087A (zh) | 包含二苯并呋喃和/或二苯并噻吩结构的杂环化合物 | |
CN108675975A (zh) | 用于有机电致发光器件的材料 | |
CN107112439A (zh) | 用于电子器件的材料 | |
CN107223122A (zh) | 用于电子器件的基于螺二芴衍生物的材料 | |
CN109963857A (zh) | 作为用于有机电致发光器件(oled)的材料的双苯并呋喃稠合的2,8-二氨基茚并[1,2-b]芴衍生物和相关化合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |