JP2010254674A - キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 - Google Patents
キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 Download PDFInfo
- Publication number
- JP2010254674A JP2010254674A JP2010074134A JP2010074134A JP2010254674A JP 2010254674 A JP2010254674 A JP 2010254674A JP 2010074134 A JP2010074134 A JP 2010074134A JP 2010074134 A JP2010074134 A JP 2010074134A JP 2010254674 A JP2010254674 A JP 2010254674A
- Authority
- JP
- Japan
- Prior art keywords
- light
- carbon atoms
- general formula
- layer
- emitting element
- 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.)
- Withdrawn
Links
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title claims abstract description 15
- 238000005286 illumination Methods 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 135
- 125000001424 substituent group Chemical group 0.000 claims description 95
- 239000000126 substance Substances 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 150000002894 organic compounds Chemical class 0.000 abstract description 34
- 230000009477 glass transition Effects 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 243
- 150000003252 quinoxalines Chemical class 0.000 description 68
- 239000000463 material Substances 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000758 substrate Substances 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- -1 halogenated quinoxaline compound Chemical class 0.000 description 24
- 238000002347 injection Methods 0.000 description 24
- 239000007924 injection Substances 0.000 description 24
- 230000005525 hole transport Effects 0.000 description 22
- 230000006870 function Effects 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 239000010408 film Substances 0.000 description 15
- 239000011159 matrix material Substances 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 238000005192 partition Methods 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 12
- 239000002131 composite material Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 238000000295 emission spectrum Methods 0.000 description 9
- 230000005284 excitation Effects 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 8
- 238000007789 sealing Methods 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 230000005281 excited state Effects 0.000 description 7
- 239000012212 insulator Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 239000005749 Copper compound Substances 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 238000006887 Ullmann reaction Methods 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 150000001880 copper compounds Chemical class 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 230000005283 ground state Effects 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- 229910052814 silicon oxide Inorganic materials 0.000 description 5
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 4
- 238000003775 Density Functional Theory Methods 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000005595 acetylacetonate group Chemical group 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group 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 3
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 3
- 0 CC[C@](C)CC=NC=*N(c(cc1)ccc1-c1c(-c(cc2)ccc2N(c2cnc[n]2)c(cc2)ccc2-[n]2c3cccc(-c4cccc5c4c(cccc4)c4[n]5-c(cc4)ccc4N(c(cc4)ccc4C4=Nc(cccc5)c5NC4c(cc4)ccc4N(c(cc4)ccc4-[n]4c5ccccc5c5c4cccc5)c4ncncc4)c4ncncc4)c3c3c2cccc3)nc(cccc2)c2n1)c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 Chemical compound CC[C@](C)CC=NC=*N(c(cc1)ccc1-c1c(-c(cc2)ccc2N(c2cnc[n]2)c(cc2)ccc2-[n]2c3cccc(-c4cccc5c4c(cccc4)c4[n]5-c(cc4)ccc4N(c(cc4)ccc4C4=Nc(cccc5)c5NC4c(cc4)ccc4N(c(cc4)ccc4-[n]4c5ccccc5c5c4cccc5)c4ncncc4)c4ncncc4)c3c3c2cccc3)nc(cccc2)c2n1)c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 3
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 3
- 229910001947 lithium oxide Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000011368 organic material Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 229910001930 tungsten oxide Inorganic materials 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [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 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 2
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 2
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- XFAPGDPYKOHYLQ-UHFFFAOYSA-N N-(4-carbazol-9-ylphenyl)-N-[4-[3-[4-(4-carbazol-9-yl-N-quinolin-8-ylanilino)phenyl]quinoxalin-2-yl]phenyl]quinolin-8-amine Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)C=2C(=NC3=CC=CC=C3N=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C3=NC=CC=C3C=CC=2)C=2C3=NC=CC=C3C=CC=2)C=C1 XFAPGDPYKOHYLQ-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000001133 acceleration Effects 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000005284 basis set Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- ADHNFLCTOCFIFV-UHFFFAOYSA-N europium(3+) 1,10-phenanthroline Chemical compound [Eu+3].c1cnc2c(c1)ccc1cccnc21 ADHNFLCTOCFIFV-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 2
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 2
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 229910003449 rhenium oxide Inorganic materials 0.000 description 2
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 229910001936 tantalum oxide Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical compound S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 2
- RTSZQXSYCGBHMO-UHFFFAOYSA-N 1,2,4-trichloro-3-prop-1-ynoxybenzene Chemical compound CC#COC1=C(Cl)C=CC(Cl)=C1Cl RTSZQXSYCGBHMO-UHFFFAOYSA-N 0.000 description 1
- XOYZGLGJSAZOAG-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-[4-[4-(n-[4-(n-phenylanilino)phenyl]anilino)phenyl]phenyl]benzene-1,4-diamine Chemical group C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 XOYZGLGJSAZOAG-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- JEBPFDQAOYARIB-UHFFFAOYSA-N 2,3,6,7-tetramethyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C=3C4=CC(C)=C(C)C=C4C(C=4C=C5C=CC=CC5=CC=4)=C4C=C(C(=CC4=3)C)C)=CC=C21 JEBPFDQAOYARIB-UHFFFAOYSA-N 0.000 description 1
- WATVCMJLZPTSSS-UHFFFAOYSA-N 2,3-bis(4-bromophenyl)quinoxaline Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2N=C1C1=CC=C(Br)C=C1 WATVCMJLZPTSSS-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- IBHNCJLKIQIKFU-UHFFFAOYSA-N 2-tert-butyl-9,10-bis(2-naphthalen-1-ylphenyl)anthracene Chemical compound C1=CC=C2C(C3=CC=CC=C3C3=C4C=CC=CC4=C(C=4C(=CC=CC=4)C=4C5=CC=CC=C5C=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=CC2=C1 IBHNCJLKIQIKFU-UHFFFAOYSA-N 0.000 description 1
- MNHPNCZSKTUPMB-UHFFFAOYSA-N 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene Chemical compound C=12C=CC=CC2=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C2=CC(C(C)(C)C)=CC=C2C=1C(C=C1)=CC=C1C1=CC=CC=C1 MNHPNCZSKTUPMB-UHFFFAOYSA-N 0.000 description 1
- ONMVVYFKZFORGI-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-1-ylanthracene Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=C(C=4C5=CC=CC=C5C=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=CC2=C1 ONMVVYFKZFORGI-UHFFFAOYSA-N 0.000 description 1
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 1
- WBPXZSIKOVBSAS-UHFFFAOYSA-N 2-tert-butylanthracene Chemical compound C1=CC=CC2=CC3=CC(C(C)(C)C)=CC=C3C=C21 WBPXZSIKOVBSAS-UHFFFAOYSA-N 0.000 description 1
- PZLZJGZGJHZQAU-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(CC)=CC=C1N1C(C=2C=CC(=CC=2)C(C)(C)C)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 PZLZJGZGJHZQAU-UHFFFAOYSA-N 0.000 description 1
- TVMBOHMLKCZFFW-UHFFFAOYSA-N 3-N,6-N,9-triphenyl-3-N,6-N-bis(9-phenylcarbazol-3-yl)carbazole-3,6-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC(=CC=C3N(C=3C=CC=CC=3)C2=CC=1)N(C=1C=CC=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 TVMBOHMLKCZFFW-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- LGDCSNDMFFFSHY-UHFFFAOYSA-N 4-butyl-n,n-diphenylaniline Polymers C1=CC(CCCC)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 LGDCSNDMFFFSHY-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- KIYZNTXHGDXHQH-UHFFFAOYSA-N 5,12-diphenyl-6,11-bis(4-phenylphenyl)tetracene Chemical compound C1=CC=CC=C1C1=CC=C(C=2C3=C(C=4C=CC=CC=4)C4=CC=CC=C4C(C=4C=CC=CC=4)=C3C(C=3C=CC(=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 KIYZNTXHGDXHQH-UHFFFAOYSA-N 0.000 description 1
- OKEZAUMKBWTTCR-AATRIKPKSA-N 5-methyl-2-[4-[(e)-2-[4-(5-methyl-1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl]-1,3-benzoxazole Chemical compound CC1=CC=C2OC(C3=CC=C(C=C3)/C=C/C3=CC=C(C=C3)C=3OC4=CC=C(C=C4N=3)C)=NC2=C1 OKEZAUMKBWTTCR-AATRIKPKSA-N 0.000 description 1
- TYGSHIPXFUQBJO-UHFFFAOYSA-N 5-n,5-n,11-n,11-n-tetrakis(4-methylphenyl)tetracene-5,11-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC3=CC=CC=C3C(N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=C2C=C2C=CC=CC2=1)C1=CC=C(C)C=C1 TYGSHIPXFUQBJO-UHFFFAOYSA-N 0.000 description 1
- USIXUMGAHVBSHQ-UHFFFAOYSA-N 9,10-bis(3,5-diphenylphenyl)anthracene Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C3=CC=CC=C3C(C=3C=C(C=C(C=3)C=3C=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=2)=C1 USIXUMGAHVBSHQ-UHFFFAOYSA-N 0.000 description 1
- YTSGZCWSEMDTBC-UHFFFAOYSA-N 9,10-bis(4-methylnaphthalen-1-yl)anthracene Chemical compound C12=CC=CC=C2C(C)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C)C2=CC=CC=C12 YTSGZCWSEMDTBC-UHFFFAOYSA-N 0.000 description 1
- BITWULPDIGXQDL-UHFFFAOYSA-N 9,10-bis[4-(2,2-diphenylethenyl)phenyl]anthracene Chemical compound C=1C=C(C=2C3=CC=CC=C3C(C=3C=CC(C=C(C=4C=CC=CC=4)C=4C=CC=CC=4)=CC=3)=C3C=CC=CC3=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 BITWULPDIGXQDL-UHFFFAOYSA-N 0.000 description 1
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 1
- OEYLQYLOSLLBTR-UHFFFAOYSA-N 9-(2-phenylphenyl)-10-[10-(2-phenylphenyl)anthracen-9-yl]anthracene Chemical group C1=CC=CC=C1C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1C1=CC=CC=C1 OEYLQYLOSLLBTR-UHFFFAOYSA-N 0.000 description 1
- SMFWPCTUTSVMLQ-UHFFFAOYSA-N 9-N,9-N,21-N,21-N-tetrakis(4-methylphenyl)-4,15-diphenylheptacyclo[12.10.1.13,7.02,12.018,25.019,24.011,26]hexacosa-1,3,5,7,9,11(26),12,14,16,18(25),19(24),20,22-tridecaene-9,21-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C2C(C=3[C]4C5=C(C=6C=CC=CC=6)C=CC6=CC(=CC([C]56)=C4C=C4C(C=5C=CC=CC=5)=CC=C2C=34)N(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=CC=1)C1=CC=C(C)C=C1 SMFWPCTUTSVMLQ-UHFFFAOYSA-N 0.000 description 1
- XCICDYGIJBPNPC-UHFFFAOYSA-N 9-[4-[3,5-bis(4-carbazol-9-ylphenyl)phenyl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=C(C=C(C=2)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 XCICDYGIJBPNPC-UHFFFAOYSA-N 0.000 description 1
- SXGIRTCIFPJUEQ-UHFFFAOYSA-N 9-anthracen-9-ylanthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C(C=3C4=CC=CC=C4C=C4C=CC=CC4=3)=C21 SXGIRTCIFPJUEQ-UHFFFAOYSA-N 0.000 description 1
- RAPHUPWIHDYTKU-WXUKJITCSA-N 9-ethyl-3-[(e)-2-[4-[4-[(e)-2-(9-ethylcarbazol-3-yl)ethenyl]phenyl]phenyl]ethenyl]carbazole Chemical compound C1=CC=C2C3=CC(/C=C/C4=CC=C(C=C4)C4=CC=C(C=C4)/C=C/C=4C=C5C6=CC=CC=C6N(C5=CC=4)CC)=CC=C3N(CC)C2=C1 RAPHUPWIHDYTKU-WXUKJITCSA-N 0.000 description 1
- NBYGJKGEGNTQBK-UHFFFAOYSA-N 9-phenyl-10-(10-phenylanthracen-9-yl)anthracene Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 NBYGJKGEGNTQBK-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- VFFVHIBDRUITTL-UHFFFAOYSA-N C(C=C1)[N-]C=C1N(c(cc1)ccc1-c1nc(cccc2)c2nc1-c(cc1)ccc1N(c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)c1cnccc1)c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 Chemical compound C(C=C1)[N-]C=C1N(c(cc1)ccc1-c1nc(cccc2)c2nc1-c(cc1)ccc1N(c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)c1cnccc1)c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 VFFVHIBDRUITTL-UHFFFAOYSA-N 0.000 description 1
- HQGYDGWWRQVQLY-UHFFFAOYSA-N C1=C(C=CC=2C3=CC=CC=C3C3(C4=CC=CC=C4C4=CC=CC=C43)C1=2)N(C1=CC=CC=C1)C1=C(C=CC=C1)C1=CC=CC=C1 Chemical group C1=C(C=CC=2C3=CC=CC=C3C3(C4=CC=CC=C4C4=CC=CC=C43)C1=2)N(C1=CC=CC=C1)C1=C(C=CC=C1)C1=CC=CC=C1 HQGYDGWWRQVQLY-UHFFFAOYSA-N 0.000 description 1
- ZKHISQHQYQCSJE-UHFFFAOYSA-N C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C(C=C(C=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C(C=C(C=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 ZKHISQHQYQCSJE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- SAOIZUHLSLDXFZ-UHFFFAOYSA-N N-[3-(9H-carbazol-1-yl)phenyl]-N,9-diphenylcarbazol-3-amine Chemical compound C1(=CC=CC=C1)N1C2=CC=CC=C2C=2C=C(C=CC1=2)N(C1=CC=CC=C1)C=1C=C(C=CC=1)C1=CC=CC=2C3=CC=CC=C3NC1=2 SAOIZUHLSLDXFZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 230000002457 bidirectional effect Effects 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- DJGAWIIYQXRUFD-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)ccc1N(c(cc1)ccc1-c1nc(cccc2)c2nc1-c(cc1)ccc1N(c(cc1)ccc1-[n]1c2cccc(-c3cccc4c3c(cccc3)c3[n]4-c(cc3)ccc3N(c(cc3)ccc3-c3nc(cccc4)c4nc3-c(cc3)ccc3N(c(cc3)ccc3-[n]3c4ccccc4c4c3cccc4)c3ccccn3)c3ncccc3)c2c2ccccc12)c1ccncc1)c1ccncc1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)ccc1N(c(cc1)ccc1-c1nc(cccc2)c2nc1-c(cc1)ccc1N(c(cc1)ccc1-[n]1c2cccc(-c3cccc4c3c(cccc3)c3[n]4-c(cc3)ccc3N(c(cc3)ccc3-c3nc(cccc4)c4nc3-c(cc3)ccc3N(c(cc3)ccc3-[n]3c4ccccc4c4c3cccc4)c3ccccn3)c3ncccc3)c2c2ccccc12)c1ccncc1)c1ccncc1 DJGAWIIYQXRUFD-UHFFFAOYSA-N 0.000 description 1
- JSRZGVVCRQPSAE-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)ccc1N(c(cc1)ccc1-c1nc(cccc2)c2nc1-c(cc1)ccc1N(c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)c1ccccn1)c1ncccc1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)ccc1N(c(cc1)ccc1-c1nc(cccc2)c2nc1-c(cc1)ccc1N(c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)c1ccccn1)c1ncccc1 JSRZGVVCRQPSAE-UHFFFAOYSA-N 0.000 description 1
- OZSRNIRFIDDNIZ-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)ccc1N(c(cc1)ccc1-c1nc(cccc2)c2nc1-c(cc1)ccc1N(c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)c1nccc2c1cccc2)c1nccc2c1cccc2 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)ccc1N(c(cc1)ccc1-c1nc(cccc2)c2nc1-c(cc1)ccc1N(c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)c1nccc2c1cccc2)c1nccc2c1cccc2 OZSRNIRFIDDNIZ-UHFFFAOYSA-N 0.000 description 1
- BHTFEVHOINTNCN-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ncc1N(c(cc1)ccc1-c1nc(cccc2)c2nc1-c(cc1)ccc1N(c(cc1)ccc1-[n]1c(cccc2)c2c2c1cccc2)c1ccc(-c2ccccc2)nc1)c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 Chemical compound c(cc1)ccc1-c(cc1)ncc1N(c(cc1)ccc1-c1nc(cccc2)c2nc1-c(cc1)ccc1N(c(cc1)ccc1-[n]1c(cccc2)c2c2c1cccc2)c1ccc(-c2ccccc2)nc1)c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 BHTFEVHOINTNCN-UHFFFAOYSA-N 0.000 description 1
- XVZOWZRMKVJEDF-UHFFFAOYSA-N c1c[nH]cc1N(c(cc1)ccc1-c1nc2ccccc2nc1-c(cc1)ccc1N(C1=CC=[N]=C1)c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)c(cc1)ccc1-[n]1c2cccc(-c3c(c(cccc4)c4[n]4-c(cc5)ccc5N(c(cc5)ccc5-c5nc(cccc6)c6nc5-c(cc5)ccc5N(c(cc5)ccc5-[n]5c(cccc6)c6c6c5cccc6)c5nccnc5)c5nccnc5)c4ccc3)c2c2c1cccc2 Chemical compound c1c[nH]cc1N(c(cc1)ccc1-c1nc2ccccc2nc1-c(cc1)ccc1N(C1=CC=[N]=C1)c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)c(cc1)ccc1-[n]1c2cccc(-c3c(c(cccc4)c4[n]4-c(cc5)ccc5N(c(cc5)ccc5-c5nc(cccc6)c6nc5-c(cc5)ccc5N(c(cc5)ccc5-[n]5c(cccc6)c6c6c5cccc6)c5nccnc5)c5nccnc5)c4ccc3)c2c2c1cccc2 XVZOWZRMKVJEDF-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000004770 chalcogenides Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- BHQBDOOJEZXHPS-UHFFFAOYSA-N ctk3i0272 Chemical group C1=CC=CC=C1C(C(=C(C=1C=CC=CC=1)C(=C1C=2C=CC=CC=2)C=2C3=CC=CC=C3C(C=3C4=CC=CC=C4C(C=4C(=C(C=5C=CC=CC=5)C(C=5C=CC=CC=5)=C(C=5C=CC=CC=5)C=4C=4C=CC=CC=4)C=4C=CC=CC=4)=C4C=CC=CC4=3)=C3C=CC=CC3=2)C=2C=CC=CC=2)=C1C1=CC=CC=C1 BHQBDOOJEZXHPS-UHFFFAOYSA-N 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000010893 electron trap Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-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
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000006872 improvement Effects 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- SRRUQKPCZKOOCR-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)quinolin-8-amine Chemical compound C1=CN=C2C(NC=3C=CC(=CC=3)N3C4=CC=CC=C4C4=CC=CC=C43)=CC=CC2=C1 SRRUQKPCZKOOCR-UHFFFAOYSA-N 0.000 description 1
- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 1
- VZYZZKOUCVXTOJ-UHFFFAOYSA-N n-[4-[4-(n-(9,9-dimethylfluoren-2-yl)anilino)phenyl]phenyl]-9,9-dimethyl-n-phenylfluoren-2-amine Chemical group C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C2C(C)(C)C3=CC=CC=C3C2=CC=1)C1=CC=CC=C1 VZYZZKOUCVXTOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- HCIIFBHDBOCSAF-UHFFFAOYSA-N octaethylporphyrin Chemical compound N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 HCIIFBHDBOCSAF-UHFFFAOYSA-N 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 238000001420 photoelectron spectroscopy Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000005381 potential energy Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 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
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- 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
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
-
- 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]
-
- 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
-
- 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
-
- 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
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
-
- 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
-
- 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
- H10K50/155—Hole transporting layers comprising dopants
-
- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
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)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
【解決手段】一般式(G1)で表されるキノキサリン誘導体を提供する。一般式(G1)で表されるキノキサリン誘導体は、バイポーラ性であり、電子輸送性および正孔輸送性の双方に優れている。また、一般式(G1)で表されるキノキサリン誘導体はガラス転移温度が高く、優れた熱的安定性を有する。また、一般式(G1)で表されるキノキサリン誘導体を用いることで、効率の良い発光素子および発光装置を得ることができる。
【選択図】なし
Description
本実施の形態では、本発明の一態様であるキノキサリン誘導体について説明する。
本実施の形態では、先の実施の形態で説明したキノキサリン誘導体を発光層に用いた発光素子の一例について、図面を参照して説明する。
開示する発明の一態様である発光素子は、複数の発光層を有するものであってもよい。複数の発光層のそれぞれから発光させることで、混合された光を得ることができる。したがって、例えば、白色光を得ることができる。本実施の形態では、複数の発光層を有する発光素子の態様について、図面を参照して説明する。
本実施の形態では、EL層を複数有する発光素子(以下、積層型素子という)について、図面を参照して説明する。
本実施の形態では、開示する発明の一態様として、発光素子を用いたパッシブマトリクス型の発光装置、およびアクティブマトリクス型の発光装置について説明する。
本実施の形態では、本発明の一態様である発光装置を用いて完成させた様々な電子機器および照明器具の一例について、図7、図8を用いて説明する。
1H NMR(CDCl3,300MHz):δ=7.11(d,J=9.8Hz,4H)、7.20−7.73(m,36H)、8.03−8.15(m,8H)
まず、ガラス基板である基板900上に、酸化珪素を含む酸化インジウム−酸化スズをスパッタリング法にて成膜し、第1の電極901を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
比較発光素子2において、発光層以外は、発光素子1と同様に形成した。以下に比較発光素子2における発光層の作製方法を示す。
102 EL層
103 第2の電極
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
201 第1の電極
203 第2の電極
211 正孔注入層
212 正孔輸送層
213 第1の発光層
214 分離層
215 第2の発光層
216 電子輸送層
217 電子注入層
301 第1の電極
302 第1のEL層
303 第2のEL層
304 第2の電極
305 電荷発生層
401 基板
402 絶縁層
403 第1の電極
404 隔壁
405 開口部
406 隔壁
407 EL層
408 第2の電極
503 走査線
505 領域
506 隔壁
508 データ線
509 接続配線
510 入力端子
511a FPC
511b FPC
512 入力端子
601 素子基板
602 画素部
603 駆動回路部
604 駆動回路部
605 シール材
606 封止基板
607 配線
608 FPC
609 nチャネル型TFT
610 pチャネル型TFT
611 スイッチング用TFT
612 電流制御用TFT
613 陽極
614 絶縁物
615 EL層
616 陰極
617 発光素子
618 空間
801 照明装置
802 照明装置
803 卓上照明器具
900 基板
901 第1の電極
902 EL層
903 第2の電極
911 第1の層
912 第2の層
913 第3の層
914 第4の層
915 第5の層
7100 テレビジョン装置
7101 筐体
7103 表示部
7105 スタンド
7107 表示部
7109 操作キー
7110 リモコン操作機
7201 本体
7202 筐体
7203 表示部
7204 キーボード
7205 外部接続ポート
7206 マウス
7301 筐体
7302 筐体
7303 連結部
7304 表示部
7305 表示部
7306 スピーカ部
7307 記録媒体挿入部
7308 LEDランプ
7309 操作キー
7310 接続端子
7311 センサ
7312 マイクロフォン
7400 携帯電話機
7401 筐体
7402 表示部
7403 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
7501 照明部
7502 傘
7503 可変アーム
7504 支柱
7505 台
7506 電源
Claims (13)
- 下記一般式(G1)で表されるキノキサリン誘導体。
(一般式(G1)において、R1〜R4はそれぞれ独立に、水素、炭素数1〜4のアルキル基、又は環を形成する炭素数が6〜10のアリール基を表す。またA1及びA2はそれぞれ独立して、水素原子、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基、又は下記一般式(A1)で表される置換基を表す。ただし、A1、A2の少なくとも一方は、一般式(A1)で表される置換基を有する。)
(一般式(A1)において、Ar1は置換又は無置換の環を形成する炭素数が4〜9のヘテロアリール基を表す。またR11〜R18はそれぞれ独立に、水素原子、炭素数1〜4のアルキル基、又は、置換もしくは無置換の環を形成する炭素数が6〜10のアリール基を表す。またJは置換もしくは無置換の炭素数6〜12のアリーレン基を表す。) - 下記一般式(G2)で表されるキノキサリン誘導体。
(一般式(G2)において、A1及びA2はそれぞれ独立して、水素原子、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基、又は下記一般式(A2)で表される置換基を表す。ただし、A1、A2の少なくとも一方は、一般式(A2)で表される置換基を有する。)
(一般式(A2)において、Ar1は置換又は無置換の環を形成する炭素数が4〜9のヘテロアリール基を表す。またR11〜R18はそれぞれ独立に、水素原子、炭素数1〜4のアルキル基、又は置換もしくは無置換の環を形成する炭素数が6〜10のアリール基を表す。またJは置換もしくは無置換の炭素数6〜12のアリーレン基を表す。) - 下記一般式(G3)で表されるキノキサリン誘導体。
(一般式(G3)において、A1、A2はそれぞれ独立して、水素原子、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基、又は下記一般式(A3)で表される置換基を表す。ただし、A1、A2の少なくとも一方は、一般式(A3)で表される置換基を有する。)
- 下記一般式(G4)で表されるキノキサリン誘導体。
(一般式(G4)において、A1及びA2はそれぞれ独立して、水素原子、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基、又は下記一般式(A4)で表される置換基を表す。ただし、A1、A2の少なくとも一方は、一般式(A4)で表される置換基を有する。)
(一般式(A4)において、Ar1は置換又は無置換の環を形成する炭素数が4〜9のヘテロアリール基を表す。またR11〜R18はそれぞれ独立に、水素原子、炭素数1〜4のアルキル基、又は、置換もしくは無置換の環を形成する炭素数が6〜10のアリール基を表す。) - 下記一般式(G5)で表されるキノキサリン誘導体。
(一般式(G5)において、A1及びA2はそれぞれ独立して、水素原子、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基、又は下記一般式(A5)で表される置換基を表す。ただし、A1、A2の少なくとも一方は、一般式(A5)で表される置換基を有する。)
(一般式(A5)において、Ar1は置換又は無置換の環を形成する炭素数が4〜9のヘテロアリール基を表す。) - 一対の電極間に、請求項1乃至請求項5のいずれか一項に記載のキノキサリン誘導体を有する発光素子。
- 一対の電極間に発光層を有し、前記発光層に請求項1乃至請求項5のいずれか一項に記載のキノキサリン誘導体を有する発光素子。
- 一対の電極間に発光層を有し、前記発光層に請求項1乃至請求項5のいずれか一項に記載のキノキサリン誘導体と蛍光を発光する物質を有する発光素子。
- 一対の電極間に発光層を有し、前記発光層に請求項1乃至請求項5のいずれか一項に記載のキノキサリン誘導体と燐光を発光する物質を有する発光素子。
- 請求項1乃至請求項5のいずれか一項に記載のキノキサリン誘導体を含む層を発光層に接して備えた発光素子。
- 請求項6乃至請求項10のいずれか一項に記載の発光素子と、前記発光素子の発光を制御する制御手段とを有する発光装置。
- 請求項11に記載の発光装置を用いた電子機器。
- 請求項11に記載の発光装置を用いた照明装置。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010074134A JP2010254674A (ja) | 2009-03-31 | 2010-03-29 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009085977 | 2009-03-31 | ||
JP2010074134A JP2010254674A (ja) | 2009-03-31 | 2010-03-29 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014186518A Division JP2015028047A (ja) | 2009-03-31 | 2014-09-12 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2010254674A true JP2010254674A (ja) | 2010-11-11 |
Family
ID=42783279
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010074134A Withdrawn JP2010254674A (ja) | 2009-03-31 | 2010-03-29 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
JP2014186518A Withdrawn JP2015028047A (ja) | 2009-03-31 | 2014-09-12 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
JP2016006940A Active JP6105099B2 (ja) | 2009-03-31 | 2016-01-18 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014186518A Withdrawn JP2015028047A (ja) | 2009-03-31 | 2014-09-12 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
JP2016006940A Active JP6105099B2 (ja) | 2009-03-31 | 2016-01-18 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
Country Status (3)
Country | Link |
---|---|
US (1) | US8313845B2 (ja) |
JP (3) | JP2010254674A (ja) |
KR (2) | KR101787733B1 (ja) |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012222249A (ja) * | 2011-04-12 | 2012-11-12 | Seiko Epson Corp | 発光素子、発光装置、認証装置および電子機器 |
JP2012222248A (ja) * | 2011-04-12 | 2012-11-12 | Seiko Epson Corp | 発光素子、発光装置、認証装置および電子機器 |
JP2012222250A (ja) * | 2011-04-12 | 2012-11-12 | Seiko Epson Corp | 発光素子、発光装置、認証装置および電子機器 |
JP2012227315A (ja) * | 2011-04-19 | 2012-11-15 | Seiko Epson Corp | 発光素子、発光装置、認証装置および電子機器 |
KR20140070365A (ko) | 2012-11-30 | 2014-06-10 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자용 정공 수송 재료 및 그것을 사용한 유기 전계 발광 소자 |
US9072150B2 (en) | 2011-04-18 | 2015-06-30 | Seiko Epson Corporation | Thiadiazole-based compound, light emitting element compound, light emitting element, light emitting device, authentication device, and electronic apparatus |
US9067952B2 (en) | 2011-08-09 | 2015-06-30 | Seiko Epson Corporation | Thiadiazole, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device |
US9159932B2 (en) | 2011-08-09 | 2015-10-13 | Seiko Epson Corporation | Light emitting element, light emitting device, and electronic device |
US9224928B2 (en) | 2011-12-28 | 2015-12-29 | Seiko Epson Corporation | Light emitting element, light emitting device and electronic apparatus |
US9324952B2 (en) | 2012-02-28 | 2016-04-26 | Seiko Epson Corporation | Thiadiazole, compound for light-emitting elements, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device |
JP2016065104A (ja) * | 2009-03-31 | 2016-04-28 | 株式会社半導体エネルギー研究所 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
US9722184B2 (en) | 2012-10-18 | 2017-08-01 | Seiko Epson Corporation | Thiadiazole, compound for light-emitting elements, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device |
US9876177B2 (en) | 2011-04-12 | 2018-01-23 | Seiko Epson Corporation | Thiadiazole-based compound, light emitting element compound, light emitting element, light emitting device, authentication device, and electronic device |
JP2019140397A (ja) * | 2011-04-29 | 2019-08-22 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、および照明装置 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI564294B (zh) | 2015-08-24 | 2017-01-01 | 國立清華大學 | 載子產生材料與有機發光二極體 |
KR102600474B1 (ko) | 2016-03-10 | 2023-11-13 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
CN110105337B (zh) * | 2019-05-31 | 2022-12-23 | 湖南大学 | 一种喹啉类三芳基胺及其制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006016384A (ja) * | 2004-06-03 | 2006-01-19 | Mitsui Chemicals Inc | アミン化合物、および該アミン化合物を含有する有機電界発光素子 |
JP2007099766A (ja) * | 2005-09-12 | 2007-04-19 | Semiconductor Energy Lab Co Ltd | キノキサリン誘導体、およびキノキサリン誘導体を用いた発光素子、発光装置、電子機器 |
JP2007284434A (ja) * | 2006-03-21 | 2007-11-01 | Semiconductor Energy Lab Co Ltd | キノキサリン誘導体、およびキノキサリン誘導体を用いた発光素子、発光装置、電子機器 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100837029B1 (ko) | 1998-09-09 | 2008-06-10 | 이데미쓰 고산 가부시키가이샤 | 유기 전자발광 소자 및 페닐렌디아민 유도체 |
JP4542646B2 (ja) | 1998-09-09 | 2010-09-15 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子およびフェニレンジアミン誘導体 |
US6503995B2 (en) * | 2000-04-12 | 2003-01-07 | Kaneka Corporation | Method of producing crosslinkable silyl group-containing polyoxyalkylene polymers |
GB0117377D0 (en) * | 2001-07-17 | 2001-09-05 | Opsys Ltd | "Tertiary diamines containing heterocyclic groups and their use in organic electroluminescent devices" |
KR101254278B1 (ko) | 2003-04-18 | 2013-04-12 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 퀴녹살린 유도체를 이용한 트랜지스터 |
EP1690866B1 (en) | 2003-12-02 | 2012-11-28 | Semiconductor Energy Laboratory Co., Ltd. | Organic metal complex and light-emitting device using same |
CN101263126B (zh) | 2005-09-12 | 2013-11-20 | 株式会社半导体能源研究所 | 喹喔啉衍生物和使用它的发光元件,发光装置及电子设备 |
WO2007108403A1 (en) * | 2006-03-21 | 2007-09-27 | Semiconductor Energy Laboratory Co., Ltd. | Quinoxaline derivative, and light-emitting element, light-emitting device, electronic device using the quinoxaline derivative |
JP2010254674A (ja) * | 2009-03-31 | 2010-11-11 | Semiconductor Energy Lab Co Ltd | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
-
2010
- 2010-03-29 JP JP2010074134A patent/JP2010254674A/ja not_active Withdrawn
- 2010-03-29 US US12/748,859 patent/US8313845B2/en active Active
- 2010-03-30 KR KR1020100028709A patent/KR101787733B1/ko active IP Right Grant
-
2014
- 2014-09-12 JP JP2014186518A patent/JP2015028047A/ja not_active Withdrawn
-
2015
- 2015-03-30 KR KR20150044620A patent/KR20150043259A/ko not_active Application Discontinuation
-
2016
- 2016-01-18 JP JP2016006940A patent/JP6105099B2/ja active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006016384A (ja) * | 2004-06-03 | 2006-01-19 | Mitsui Chemicals Inc | アミン化合物、および該アミン化合物を含有する有機電界発光素子 |
JP2007099766A (ja) * | 2005-09-12 | 2007-04-19 | Semiconductor Energy Lab Co Ltd | キノキサリン誘導体、およびキノキサリン誘導体を用いた発光素子、発光装置、電子機器 |
JP2007284434A (ja) * | 2006-03-21 | 2007-11-01 | Semiconductor Energy Lab Co Ltd | キノキサリン誘導体、およびキノキサリン誘導体を用いた発光素子、発光装置、電子機器 |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016065104A (ja) * | 2009-03-31 | 2016-04-28 | 株式会社半導体エネルギー研究所 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
JP2012222248A (ja) * | 2011-04-12 | 2012-11-12 | Seiko Epson Corp | 発光素子、発光装置、認証装置および電子機器 |
JP2012222250A (ja) * | 2011-04-12 | 2012-11-12 | Seiko Epson Corp | 発光素子、発光装置、認証装置および電子機器 |
US9876177B2 (en) | 2011-04-12 | 2018-01-23 | Seiko Epson Corporation | Thiadiazole-based compound, light emitting element compound, light emitting element, light emitting device, authentication device, and electronic device |
JP2012222249A (ja) * | 2011-04-12 | 2012-11-12 | Seiko Epson Corp | 発光素子、発光装置、認証装置および電子機器 |
US9072150B2 (en) | 2011-04-18 | 2015-06-30 | Seiko Epson Corporation | Thiadiazole-based compound, light emitting element compound, light emitting element, light emitting device, authentication device, and electronic apparatus |
JP2012227315A (ja) * | 2011-04-19 | 2012-11-15 | Seiko Epson Corp | 発光素子、発光装置、認証装置および電子機器 |
JP2019140397A (ja) * | 2011-04-29 | 2019-08-22 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、および照明装置 |
US9067952B2 (en) | 2011-08-09 | 2015-06-30 | Seiko Epson Corporation | Thiadiazole, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device |
US9159932B2 (en) | 2011-08-09 | 2015-10-13 | Seiko Epson Corporation | Light emitting element, light emitting device, and electronic device |
US9741940B2 (en) | 2011-08-09 | 2017-08-22 | Seiko Epson Corporation | Thiadiazole, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device |
US9401460B2 (en) | 2011-12-28 | 2016-07-26 | Seiko Epson Corporation | Light emitting element |
US9224928B2 (en) | 2011-12-28 | 2015-12-29 | Seiko Epson Corporation | Light emitting element, light emitting device and electronic apparatus |
US9324952B2 (en) | 2012-02-28 | 2016-04-26 | Seiko Epson Corporation | Thiadiazole, compound for light-emitting elements, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device |
US9722184B2 (en) | 2012-10-18 | 2017-08-01 | Seiko Epson Corporation | Thiadiazole, compound for light-emitting elements, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device |
US9269910B2 (en) | 2012-11-30 | 2016-02-23 | Samsung Display Co., Ltd. | Substituted carbazoles as hole transport materials for organic electroluminescence devices and organic electroluminescence devices comprising the same |
KR20140070365A (ko) | 2012-11-30 | 2014-06-10 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자용 정공 수송 재료 및 그것을 사용한 유기 전계 발광 소자 |
Also Published As
Publication number | Publication date |
---|---|
US8313845B2 (en) | 2012-11-20 |
KR20150043259A (ko) | 2015-04-22 |
US20100244671A1 (en) | 2010-09-30 |
JP2015028047A (ja) | 2015-02-12 |
KR101787733B1 (ko) | 2017-10-18 |
KR20100109509A (ko) | 2010-10-08 |
JP2016065104A (ja) | 2016-04-28 |
JP6105099B2 (ja) | 2017-03-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6105099B2 (ja) | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 | |
JP6314184B2 (ja) | 発光素子、発光装置、電子機器及び照明装置 | |
JP6026613B2 (ja) | 発光素子、発光装置、電子機器、照明装置 | |
KR101670036B1 (ko) | 벤조옥사졸 유도체, 벤조옥사졸 유도체를 이용한 발광소자, 발광장치 및 전자기기 | |
KR101389522B1 (ko) | 퀴녹살린 유도체, 및 퀴녹살린 유도체를 사용한 발광소자, 발광장치, 전자기기 | |
JP5547529B2 (ja) | オキサジアゾール誘導体、発光素子、表示装置、照明装置、及び電子機器 | |
JP5855220B2 (ja) | 発光素子 | |
JP6099781B2 (ja) | 発光素子、発光装置、照明装置、電子機器 | |
JP5996181B2 (ja) | ベンゾオキサゾール誘導体 | |
KR20100101668A (ko) | 트리아졸 유도체, 발광 소자, 발광 장치, 및 전자기기 | |
JP5590909B2 (ja) | オキサジアゾール誘導体、オキサジアゾール誘導体を用いた発光素子、および発光装置 | |
JP5770977B2 (ja) | オキサジアゾール誘導体、オキサジアゾール誘導体を用いた発光素子、発光装置、電子機器、および照明装置 | |
JP2010222288A (ja) | カルバゾール誘導体、カルバゾール誘導体を用いた発光素子、発光装置、電子機器および照明装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20130213 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140701 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20140725 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140811 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20140902 |
|
A761 | Written withdrawal of application |
Free format text: JAPANESE INTERMEDIATE CODE: A761 Effective date: 20140916 |