JP2022532949A - 窒素含有化合物、電子部品及び電子装置 - Google Patents
窒素含有化合物、電子部品及び電子装置 Download PDFInfo
- Publication number
- JP2022532949A JP2022532949A JP2021572911A JP2021572911A JP2022532949A JP 2022532949 A JP2022532949 A JP 2022532949A JP 2021572911 A JP2021572911 A JP 2021572911A JP 2021572911 A JP2021572911 A JP 2021572911A JP 2022532949 A JP2022532949 A JP 2022532949A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- nitrogen
- containing compound
- groups
- 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.)
- Granted
Links
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims abstract description 10
- -1 nitrogen-containing compound Chemical class 0.000 claims abstract description 90
- 125000004432 carbon atom Chemical group C* 0.000 claims description 201
- 239000010410 layer Substances 0.000 claims description 124
- 125000003118 aryl group Chemical group 0.000 claims description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 50
- 238000005401 electroluminescence Methods 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 230000000903 blocking effect Effects 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 239000002346 layers by function Substances 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000005104 aryl silyl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000006836 terphenylene group Chemical group 0.000 claims description 2
- 239000011368 organic material Substances 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 238000006243 chemical reaction Methods 0.000 description 66
- 239000000543 intermediate Substances 0.000 description 36
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 33
- 239000000463 material Substances 0.000 description 32
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 31
- 239000000203 mixture Substances 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 24
- 239000012043 crude product Substances 0.000 description 22
- 230000005525 hole transport Effects 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 229910001873 dinitrogen Inorganic materials 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 229940125904 compound 1 Drugs 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 14
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 13
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000004949 mass spectrometry Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 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 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 7
- 125000005259 triarylamine group Chemical group 0.000 description 7
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 230000021615 conjugation Effects 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000005264 aryl amine group Chemical group 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 description 3
- 150000002830 nitrogen compounds Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
- GTKHJVYKTOLTPB-UHFFFAOYSA-N 2-bromo-7-chloro-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC(Cl)=CC=C3C2=C1 GTKHJVYKTOLTPB-UHFFFAOYSA-N 0.000 description 2
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- FDPBPKDNWCZVQR-UHFFFAOYSA-N 3-bromodibenzothiophene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3SC2=C1 FDPBPKDNWCZVQR-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- PYHZXOYNICJOTG-UHFFFAOYSA-N [2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P PYHZXOYNICJOTG-UHFFFAOYSA-N 0.000 description 2
- FVKZNRXWZCBUPY-UHFFFAOYSA-N [4-(4-chlorophenyl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=C(Cl)C=C1 FVKZNRXWZCBUPY-UHFFFAOYSA-N 0.000 description 2
- GFGRAWRKLIXQAQ-UHFFFAOYSA-N [Zn].[Zn].[In] Chemical compound [Zn].[Zn].[In] GFGRAWRKLIXQAQ-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 125000005649 substituted arylene group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- AFVDZBIIBXWASR-AATRIKPKSA-N (E)-1,3,5-hexatriene Chemical compound C=C\C=C\C=C AFVDZBIIBXWASR-AATRIKPKSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JSVXIWLDFVOHBB-UHFFFAOYSA-N 1-bromo-2-(2-chlorophenyl)benzene Chemical group ClC1=CC=CC=C1C1=CC=CC=C1Br JSVXIWLDFVOHBB-UHFFFAOYSA-N 0.000 description 1
- SOODLDGRGXOSTA-UHFFFAOYSA-N 2-bromo-9-phenylcarbazole Chemical compound C=1C(Br)=CC=C(C2=CC=CC=C22)C=1N2C1=CC=CC=C1 SOODLDGRGXOSTA-UHFFFAOYSA-N 0.000 description 1
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- IYKFYARMMIESOX-SPJNRGJMSA-N adamantanone Chemical compound C([C@H](C1)C2)[C@H]3C[C@@H]1C(=O)[C@@H]2C3 IYKFYARMMIESOX-SPJNRGJMSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000006193 alkinyl group Chemical group 0.000 description 1
- 125000002521 alkyl halide group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
- 230000005281 excited state Effects 0.000 description 1
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 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
- 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
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 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
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- 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
- C07C211/54—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 two or three six-membered aromatic rings
-
- 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
- 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
-
- 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
- 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
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
-
- 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
-
- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- 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
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
-
- 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
- H10K50/181—Electron blocking layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Photovoltaic Devices (AREA)
Abstract
Description
Ar1及びAr2は、同一でも異なっていても良く、且つ、それぞれ独立に、置換若しくは無置換の炭素原子数6~20のアリール基、置換若しくは無置換の炭素原子数1~20のヘテロアリール基から選ばれ、
前記Ar1、Ar2及びLの置換基は、同一でも異なっていても良く、それぞれ独立に、二重水素、ニトロ基、ヒドロキシ基、アルキル基、シクロアルキル基、アルケニル基、アルキニル基、ヘテロシクロアルキル基、アルコキシ基、アルキルアミノ基、アリールアミノ基、アルキルチオ基、アリールシリル基から選ばれる。
Ar1及びAr2は、同一でも異なっていても良く、且つ、それぞれ独立に、置換若しくは無置換の炭素原子数6~20のアリール基、置換若しくは無置換の炭素原子数1~20のヘテロアリール基から選ばれ、
前記Ar1、Ar2及びLの置換基は、同一でも異なっていても良く、それぞれ独立に、二重水素、ニトロ基、ヒドロキシ基、アルキル基、シクロアルキル基、アルケニル基、アルキニル基、ヘテロシクロアルキル基、アルコキシ基、アルキルアミノ基、アリールアミノ基、アルキルチオ基、アリールシリル基から選ばれる。
E1~E11は、それぞれ独立に、水素、炭素原子数3~20のヘテロアリール基、炭素原子数6~20のアリール基、炭素原子数8~12のアリールシリル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基、炭素原子数1~10のアルコキシ基、炭素原子数1~10のアルキルチオ基から選ばれ、
erは、置換基Erの数であり、rは、1~11の任意の整数であり、rが1、2、3、4、5又は6から選ばれる場合、erは、1、2、3又は4から選ばれ、rが7又は10から選ばれる場合、erは、1、2、3、4、5又は6から選ばれ、rが8又は9から選ばれる場合、erは、1、2、3、4、5、6、7又は8から選ばれ、erが1より大きい場合、任意の2つのErは、同一でも異なっていても良く、
K3は、C(E12E13)から選ばれ、ここで、E12、E13は、それぞれ独立に、フェニル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基から選ばれる。
G1~G5は、それぞれ独立に、N又はC(F1)から選ばれ、且つG1~G5のうちの少なくとも1つは、Nから選ばれる;G1~G5のうちの2つ以上がC(F1)から選ばれる場合、任意の2つのF1は、同一でも異なっていても良い。
G6~G13は、それぞれ独立に、N又はC(F2)から選ばれ、且つG6~G13のうちの少なくとも1つは、Nから選ばれる;G6~G13のうちの2つ以上がC(F2)から選ばれる場合、任意の2つのF2は、同一でも異なっていても良い。
G14~G23は、それぞれ独立に、N又はC(F3)から選ばれ、且つG14~G23のうちの少なくとも1つは、Nから選ばれる;G14~G23のうちの2つ以上がC(F3)から選ばれる場合、任意の2つのF3は、同一でも異なっていても良い。
G24~G33は、それぞれ独立に、N又はC(F4)から選ばれ、且つG24~G33のうちの少なくとも1つは、Nから選ばれる;G24~G33のうちの2つ以上がC(F4)から選ばれる場合、任意の2つのF4は、同一でも異なっていても良い。
R1は、水素、二重水素、炭素原子数8~12のアリールシリル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基、炭素原子数1~10のアルコキシ基、炭素原子数1~10のアルキルチオ基から選ばれ、
R2~R9、R21は、それぞれ独立に、水素、二重水素、炭素原子数3~10のヘテロアリール基、炭素原子数8~12のアリールシリル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基、炭素原子数1~10のアルコキシ基、炭素原子数1~10のアルキルチオ基から選ばれ、
R10~R20、F1~F4は、それぞれ独立に、水素、二重水素、炭素原子数6~12のアリール基、炭素原子数3~10のヘテロアリール基、炭素原子数8~12のアリールシリル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基、炭素原子数1~10のアルコキシ基、炭素原子数1~10のアルキルチオ基から選ばれ、
hkは、置換基Rkの数であり、kは、1~21の任意の整数であり、ここで、kが5又は17から選ばれる場合、hkは、1、2又は3から選ばれ、kが2、7、8、12、15、16、18又は21から選ばれる場合、hkは、1、2、3又は4から選ばれ、kが1、3、4、6、9又は14から選ばれる場合、hkは、1、2、3、4又は5から選ばれ、kが13である場合、hkは、1、2、3、4、5又は6から選ばれ、kが10又は19から選ばれる場合、hkは、1、2、3、4、5、6又は7から選ばれ、kが20から選ばれる場合、hkは、1、2、3、4、5、6、7又は8から選ばれ、kが11である場合、hkは、1、2、3、4、5、6、7、8又は9から選ばれ、hkが1より大きい場合、任意の2つのRkは、同一でも異なっていても良く、
K1は、O、S、Se、N(R22)、C(R23R24)、Si(R25R26)から選ばれ、ここで、R22~R26は、それぞれ独立に、フェニル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基から選ばれ、
K2は、単結合、O、S、Se、N(R27)、C(R28R29)、Si(R30R31)から選ばれ、ここで、R27~R31は、それぞれ独立に、フェニル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基から選ばれる。
以下のような方法により青色有機エレクトロルミネッセンスデバイスを製造した。
Claims (18)
- 構造が式Iで示されるものである窒素含有化合物であって、
Ar1及びAr2は、同一でも異なっていても良く、且つ、それぞれ独立に、置換若しくは無置換の炭素原子数6~20のアリール基、置換若しくは無置換の炭素原子数1~20のヘテロアリール基から選ばれ、
前記Ar1、Ar2及びLの置換基は、同一でも異なっていても良く、それぞれ独立に、二重水素、ニトロ基、ヒドロキシ基、アルキル基、シクロアルキル基、アルケニル基、アルキニル基、ヘテロシクロアルキル基、アルコキシ基、アルキルアミノ基、アリールアミノ基、アルキルチオ基、アリールシリル基から選ばれることを特徴とする窒素含有化合物。 - 前記Lは、単結合、置換若しくは無置換のフェニレン基、置換若しくは無置換のナフチレン基、置換若しくは無置換のビフェニレン基、置換若しくは無置換のターフェニレン基、置換若しくは無置換のジメチルフルオレニリデン基から選ばれることを特徴とする請求項1に記載の窒素含有化合物。
- 前記Lは、置換若しくは無置換のフェナントリレン基から選ばれることを特徴とする請求項1に記載の窒素含有化合物。
- Lは、単結合から選ばれ、又は、化学式j-1~化学式j-7で示される基からなる群から選ばれ、
E1~E11は、それぞれ独立に、水素、炭素原子数3~20のヘテロアリール基、炭素原子数6~20のアリール基、炭素原子数8~12のアリールシリル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基、炭素原子数1~10のアルコキシ基、炭素原子数1~10のアルキルチオ基から選ばれ、
erは、置換基Erの数であり、rは、1~11の任意の整数であり、rが1、2、3、4、5又は6から選ばれる場合、erは、1、2、3又は4から選ばれ、rが7又は10から選ばれる場合、erは、1、2、3、4、5又は6から選ばれ、rが8又は9から選ばれる場合、erは、1、2、3、4、5、6、7又は8から選ばれ、erが1より大きい場合、任意の2つのErは、同一でも異なっていても良く、
K3は、C(E12E13)から選ばれ、ここで、E12、E13は、それぞれ独立に、フェニル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基から選ばれることを特徴とする請求項1に記載の窒素含有化合物。 - Ar1及びAr2は、それぞれ独立に、以下の基からなる群から選ばれ、
G1~G5は、それぞれ独立に、N又はC(F1)から選ばれ、且つG1~G5のうちの少なくとも1つは、Nから選ばれる;G1~G5のうちの2つ以上がC(F1)から選ばれる場合、任意の2つのF1は、同一でも異なっていても良く、
G6~G13は、それぞれ独立に、N又はC(F2)から選ばれ、且つG6~G13のうちの少なくとも1つは、Nから選ばれる;G6~G13のうちの2つ以上がC(F2)から選ばれる場合、任意の2つのF2は、同一でも異なっていても良く、
G14~G23は、それぞれ独立に、N又はC(F3)から選ばれ、且つG14~G23のうちの少なくとも1つは、Nから選ばれる;G14~G23のうちの2つ以上がC(F3)から選ばれる場合、任意の2つのF3は、同一でも異なっていても良く、
G24~G33は、それぞれ独立に、N又はC(F4)から選ばれ、且つG24~G33のうちの少なくとも1つは、Nから選ばれる;G24~G33のうちの2つ以上がC(F4)から選ばれる場合、任意の2つのF4は、同一でも異なっていても良く、
R1は、水素、二重水素、炭素原子数8~12のアリールシリル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基、炭素原子数1~10のアルコキシ基、炭素原子数1~10のアルキルチオ基から選ばれ、
R2~R9、R21は、それぞれ独立に、水素、二重水素、炭素原子数3~10のヘテロアリール基、炭素原子数8~12のアリールシリル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基、炭素原子数1~10のアルコキシ基、炭素原子数1~10のアルキルチオ基から選ばれ、
R10~R20、F1~F4は、それぞれ独立に、水素、二重水素、炭素原子数6~12のアリール基、炭素原子数3~10のヘテロアリール基、炭素原子数8~12のアリールシリル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基、炭素原子数1~10のアルコキシ基、炭素原子数1~10のアルキルチオ基から選ばれ、
hkは、置換基Rkの数であり、kは、1~21の任意の整数であり、ここで、kが5又は17から選ばれる場合、hkは、1、2又は3から選ばれ、kが2、7、8、12、15、16、18又は21から選ばれる場合、hkは、1、2、3又は4から選ばれ、kが1、3、4、6、9又は14から選ばれる場合、hkは、1、2、3、4又は5から選ばれ、kが13である場合、hkは、1、2、3、4、5又は6から選ばれ、kが10又は19から選ばれる場合、hkは、1、2、3、4、5、6又は7から選ばれ、kが20から選ばれる場合、hkは、1、2、3、4、5、6、7又は8から選ばれ、kが11である場合、hkは、1、2、3、4、5、6、7、8又は9から選ばれ、hkが1より大きい場合、任意の2つのRkは、同一でも異なっていても良く、
K1は、O、S、Se、N(R22)、C(R23R24)、Si(R25R26)から選ばれ、ここで、R22~R26は、それぞれ独立に、フェニル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基から選ばれ、
K2は、単結合、O、S、Se、N(R27)、C(R28R29)、Si(R30R31)から選ばれ、ここで、R27~R31は、それぞれ独立に、フェニル基、炭素原子数1~10のアルキル基、炭素原子数2~6のアルケニル基、炭素原子数2~6のアルキニル基、炭素原子数3~10のシクロアルキル基、炭素原子数2~10のヘテロシクロアルキル基から選ばれることを特徴とする請求項1に記載の窒素含有化合物。 - Ar1及びAr2は、同一でも異なっていても良く、且つ、それぞれ独立に、置換若しくは無置換の炭素原子数6~20のアリール基、置換若しくは無置換の炭素原子数7~20のヘテロアリール基から選ばれることを特徴とする請求項1に記載の窒素含有化合物。
- 前記Ar1及びAr2は、同一でも異なっていても良く、且つ、それぞれ独立に、炭素原子数6~20の無置換のアリール基、炭素原子数15~20の置換のアリール基、炭素原子数12~18の無置換のヘテロアリール基から選ばれることを特徴とする請求項1に記載の窒素含有化合物。
- 対向に設けられる陽極及び陰極と、前記陽極と前記陰極との間に設けられる機能層と、を含み、
前記機能層は、請求項1から請求項14のいずれか1項に記載の窒素含有化合物を含むことを特徴とする電子部品。 - 前記機能層は、請求項1から請求項14のいずれか1項に記載の窒素含有化合物を含む電子阻止層を含むことを特徴とする請求項15に記載の電子部品。
- 前記電子部品は、有機エレクトロルミネッセンスデバイス又は太陽電池であることを特徴とする請求項15又は16に記載の電子部品。
- 請求項15から請求項17のいずれか1項に記載の電子部品を含むことを特徴とする電子装置。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201911054970.9 | 2019-10-31 | ||
CN201911054970 | 2019-10-31 | ||
CN201911121665.7A CN111138297B (zh) | 2019-10-31 | 2019-11-15 | 含氮化合物、电子元件和电子装置 |
CN201911121665.7 | 2019-11-15 | ||
PCT/CN2020/099783 WO2021082504A1 (zh) | 2019-10-31 | 2020-07-01 | 含氮化合物、电子元件和电子装置 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2022532949A true JP2022532949A (ja) | 2022-07-20 |
JP7105388B1 JP7105388B1 (ja) | 2022-07-22 |
Family
ID=70517092
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021572911A Active JP7105388B1 (ja) | 2019-10-31 | 2020-07-01 | 窒素含有化合物、電子部品及び電子装置 |
Country Status (5)
Country | Link |
---|---|
US (1) | US11098022B2 (ja) |
EP (1) | EP3826080B1 (ja) |
JP (1) | JP7105388B1 (ja) |
CN (1) | CN111138297B (ja) |
WO (1) | WO2021082504A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111138297B (zh) | 2019-10-31 | 2021-01-08 | 陕西莱特光电材料股份有限公司 | 含氮化合物、电子元件和电子装置 |
CN112759582B (zh) * | 2020-06-05 | 2023-04-18 | 陕西莱特光电材料股份有限公司 | 一种含氮化合物以及使用其的电子元件和电子装置 |
CN113173858B (zh) | 2021-04-21 | 2022-03-11 | 陕西莱特迈思光电材料有限公司 | 含氮化合物、电子元件和电子装置 |
CN117126132A (zh) * | 2021-06-24 | 2023-11-28 | 陕西莱特光电材料股份有限公司 | 有机化合物、电子元件和电子装置 |
CN117384047A (zh) * | 2023-02-20 | 2024-01-12 | 陕西莱特光电材料股份有限公司 | 有机化合物及包含其的有机电致发光器件和电子装置 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20190035567A (ko) * | 2017-09-25 | 2019-04-03 | 머티어리얼사이언스 주식회사 | 유기 화합물 및 이를 포함하는 유기전계발광 소자 |
CN110128279A (zh) * | 2019-06-14 | 2019-08-16 | 陕西莱特光电材料股份有限公司 | 有机电致发光材料及包含该材料的有机电致发光器件 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130112850A (ko) * | 2010-06-07 | 2013-10-14 | 호도가야 가가쿠 고교 가부시키가이샤 | 아크리단환 구조를 가지는 화합물 및 유기 일렉트로 루미네센스 소자 |
KR102148643B1 (ko) * | 2013-09-26 | 2020-08-28 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
CN105829279B (zh) * | 2013-12-26 | 2018-06-08 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含其的有机电致发光装置 |
KR102587380B1 (ko) * | 2015-12-10 | 2023-10-12 | 솔루스첨단소재 주식회사 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR102587381B1 (ko) * | 2015-12-21 | 2023-10-12 | 솔루스첨단소재 주식회사 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101917953B1 (ko) * | 2016-06-02 | 2018-11-13 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
KR102295572B1 (ko) | 2017-04-07 | 2021-08-30 | 코웨이 주식회사 | 안마볼과 독립적으로 구동되는 별도의 발열체를 구비하는 안마의자용 발열 조립체 |
CN108083969B (zh) * | 2017-12-21 | 2020-10-09 | 湖南大学 | 螺茚化合物及其制备和应用 |
KR102230983B1 (ko) * | 2018-04-10 | 2021-03-23 | 주식회사 엘지화학 | 다환 화합물 및 이를 포함하는 유기 발광 소자 |
US20210130295A1 (en) * | 2018-09-04 | 2021-05-06 | Lg Chem, Ltd. | Compound and organic light emitting device comprising the same |
KR20200037732A (ko) * | 2018-10-01 | 2020-04-09 | 머티어리얼사이언스 주식회사 | 유기 화합물 및 이를 포함하는 유기전계발광소자 |
CN109535011B (zh) * | 2018-12-24 | 2021-11-16 | 陕西莱特迈思光电材料有限公司 | 有机电致发光材料及包含其的有机电致发光器件 |
CN110183333B (zh) * | 2019-06-19 | 2020-06-30 | 陕西莱特光电材料股份有限公司 | 一种有机电致发光材料及包含该材料的有机电致发光器件 |
CN110240546B (zh) * | 2019-06-24 | 2020-04-17 | 陕西莱特光电材料股份有限公司 | 一种含金刚烷基的三苯胺类衍生物的制备方法 |
CN111138297B (zh) * | 2019-10-31 | 2021-01-08 | 陕西莱特光电材料股份有限公司 | 含氮化合物、电子元件和电子装置 |
-
2019
- 2019-11-15 CN CN201911121665.7A patent/CN111138297B/zh active Active
-
2020
- 2020-07-01 JP JP2021572911A patent/JP7105388B1/ja active Active
- 2020-07-01 WO PCT/CN2020/099783 patent/WO2021082504A1/zh active Application Filing
- 2020-09-18 US US17/025,569 patent/US11098022B2/en active Active
- 2020-09-24 EP EP20198011.7A patent/EP3826080B1/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20190035567A (ko) * | 2017-09-25 | 2019-04-03 | 머티어리얼사이언스 주식회사 | 유기 화합물 및 이를 포함하는 유기전계발광 소자 |
CN110128279A (zh) * | 2019-06-14 | 2019-08-16 | 陕西莱特光电材料股份有限公司 | 有机电致发光材料及包含该材料的有机电致发光器件 |
Also Published As
Publication number | Publication date |
---|---|
US20210130313A1 (en) | 2021-05-06 |
WO2021082504A1 (zh) | 2021-05-06 |
JP7105388B1 (ja) | 2022-07-22 |
CN111138297A (zh) | 2020-05-12 |
EP3826080B1 (en) | 2022-05-11 |
EP3826080A1 (en) | 2021-05-26 |
CN111138297B (zh) | 2021-01-08 |
US11098022B2 (en) | 2021-08-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3845522A1 (en) | Nitrogen-containing compound, electronic element and electronic device | |
EP3978475B1 (en) | Compound, photoelectric conversion device, and electronic device | |
KR102466473B1 (ko) | 질소 함유 화합물, 이를 포함하는 전자 소자 및 전자 장치 | |
EP2924020B1 (en) | Fluoranthene compound, and organic electronic device comprising same | |
CN112250701B (zh) | 一种有机化合物以及使用其的电子元件和电子装置 | |
JP7105388B1 (ja) | 窒素含有化合物、電子部品及び電子装置 | |
CN113717059B (zh) | 一种有机化合物及包含其的电子元件和电子装置 | |
KR102363659B1 (ko) | 질소 함유 화합물, 전자 소자 및 전자 장치 | |
WO2021135516A1 (zh) | 有机化合物、电子元件和电子装置 | |
CN113735861B (zh) | 有机化合物及使用其的电子元件和电子装置 | |
CN113861044B (zh) | 有机化合物及包含其的电子元件和电子装置 | |
CN115521214B (zh) | 有机化合物及包含其的电子元件和电子装置 | |
CN115784904A (zh) | 含氮化合物和电子元件及电子装置 | |
CN114133351B (zh) | 含氮化合物及包含其的电子元件和电子装置 | |
CN113380954A (zh) | 有机电致发光器件及电子装置 | |
CN115650899B (zh) | 含氮化合物、电子元件和电子装置 | |
CN116444384A (zh) | 有机化合物、有机电致发光器件和电子装置 | |
CN114181166B (zh) | 有机化合物及包含其的电子元件和电子装置 | |
CN113896720B (zh) | 有机化合物、电子元件及电子装置 | |
CN115557937A (zh) | 含氮化合物及包含其的有机电致发光器件和电子装置 | |
CN115521212A (zh) | 有机材料、电子元件和电子装置 | |
CN113782689A (zh) | 用于有机光电装置的组合物、有机光电装置及显示装置 | |
KR20220016500A (ko) | 질소 함유 화합물, 전자 소자 및 전자 장치 | |
CN115490693B (zh) | 有机化合物以及包含其的电子元件和电子装置 | |
CN114497424B (zh) | 有机电致发光器件及包括其的电子装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20211208 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20211208 |
|
A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20211208 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20220614 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20220711 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7105388 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |