JP2013012698A - 複合材料、発光素子、発光装置、電子機器、及び照明装置 - Google Patents
複合材料、発光素子、発光装置、電子機器、及び照明装置 Download PDFInfo
- Publication number
- JP2013012698A JP2013012698A JP2011219738A JP2011219738A JP2013012698A JP 2013012698 A JP2013012698 A JP 2013012698A JP 2011219738 A JP2011219738 A JP 2011219738A JP 2011219738 A JP2011219738 A JP 2011219738A JP 2013012698 A JP2013012698 A JP 2013012698A
- Authority
- JP
- Japan
- Prior art keywords
- light
- substituted
- group
- unsubstituted
- composite material
- 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- Withdrawn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
- 239000002131 composite material Substances 0.000 title claims abstract description 257
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 106
- 150000002484 inorganic compounds Chemical class 0.000 claims abstract description 70
- 229910010272 inorganic material Inorganic materials 0.000 claims abstract description 69
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims abstract description 58
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims abstract description 46
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 131
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 108
- 239000000126 substance Substances 0.000 claims description 89
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
- -1 dibenzofuranyl group Chemical group 0.000 claims description 53
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 229910000314 transition metal oxide Inorganic materials 0.000 claims description 21
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000005561 phenanthryl group Chemical group 0.000 claims description 10
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 10
- 229910052717 sulfur Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000005580 triphenylene group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 238000001420 photoelectron spectroscopy Methods 0.000 claims description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 5
- 230000001747 exhibiting effect Effects 0.000 claims description 5
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 5
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 5
- 229910001935 vanadium oxide Inorganic materials 0.000 claims description 5
- 238000005286 illumination Methods 0.000 claims description 4
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 claims description 4
- 229910003449 rhenium oxide Inorganic materials 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 3
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 3
- 229910000449 hafnium oxide Inorganic materials 0.000 claims description 3
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 3
- 229910001925 ruthenium oxide Inorganic materials 0.000 claims description 3
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims description 3
- 229910001923 silver oxide Inorganic materials 0.000 claims description 3
- 229910001936 tantalum oxide Inorganic materials 0.000 claims description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 3
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 3
- 238000002347 injection Methods 0.000 abstract description 101
- 239000007924 injection Substances 0.000 abstract description 101
- 239000000463 material Substances 0.000 abstract description 81
- 238000012546 transfer Methods 0.000 abstract description 68
- 230000003993 interaction Effects 0.000 abstract description 65
- 150000002894 organic compounds Chemical class 0.000 abstract description 46
- 238000010521 absorption reaction Methods 0.000 abstract description 34
- 239000000243 solution Substances 0.000 abstract description 9
- 239000010410 layer Substances 0.000 description 322
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 156
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 120
- 239000000203 mixture Substances 0.000 description 61
- 239000000758 substrate Substances 0.000 description 55
- 230000000052 comparative effect Effects 0.000 description 50
- 238000005481 NMR spectroscopy Methods 0.000 description 48
- 230000005525 hole transport Effects 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 238000005401 electroluminescence Methods 0.000 description 42
- 229910052757 nitrogen Inorganic materials 0.000 description 41
- 238000000034 method Methods 0.000 description 40
- 230000031700 light absorption Effects 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 34
- 239000000706 filtrate Substances 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- 238000005259 measurement Methods 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- 238000000862 absorption spectrum Methods 0.000 description 25
- 239000000843 powder Substances 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 230000006870 function Effects 0.000 description 22
- 238000004809 thin layer chromatography Methods 0.000 description 22
- 239000012299 nitrogen atmosphere Substances 0.000 description 21
- 238000004770 highest occupied molecular orbital Methods 0.000 description 20
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 20
- 238000002835 absorbance Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 239000012298 atmosphere Substances 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 16
- 238000010549 co-Evaporation Methods 0.000 description 16
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 14
- 238000010898 silica gel chromatography Methods 0.000 description 14
- 238000001308 synthesis method Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 239000000872 buffer Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000000859 sublimation Methods 0.000 description 12
- 230000008022 sublimation Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000002194 synthesizing effect Effects 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000012046 mixed solvent Substances 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 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 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- 238000001362 electron spin resonance spectrum Methods 0.000 description 10
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 10
- 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 9
- 238000004435 EPR spectroscopy Methods 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 150000004820 halides Chemical class 0.000 description 9
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 9
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 238000007740 vapor deposition Methods 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- OOKRYIPMHLUQHU-UHFFFAOYSA-N 9-(4-bromophenyl)-9-phenylfluorene Chemical compound C1=CC(Br)=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 OOKRYIPMHLUQHU-UHFFFAOYSA-N 0.000 description 7
- 125000005595 acetylacetonate group Chemical group 0.000 description 7
- 150000004696 coordination complex Chemical class 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 7
- 239000011159 matrix material Substances 0.000 description 7
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 7
- 238000007789 sealing Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 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 6
- 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 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000004544 sputter deposition Methods 0.000 description 6
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 6
- JEYLGFCAZBGCMC-UHFFFAOYSA-N 3-(4-bromophenyl)-9-phenylcarbazole Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 JEYLGFCAZBGCMC-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 238000009825 accumulation Methods 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 5
- 229910003437 indium oxide Inorganic materials 0.000 description 5
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 229920000767 polyaniline Polymers 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 239000011787 zinc oxide Substances 0.000 description 5
- 229960001296 zinc oxide Drugs 0.000 description 5
- 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 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 125000005577 anthracene group Chemical group 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 230000000295 complement effect Effects 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 4
- 229910001947 lithium oxide Inorganic materials 0.000 description 4
- 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 4
- 150000002909 rare earth metal compounds Chemical class 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 239000000565 sealant 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
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000005092 sublimation method Methods 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- DRKHIWKXLZCAKP-UHFFFAOYSA-N 1-bromo-2-(2-bromophenyl)benzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1Br DRKHIWKXLZCAKP-UHFFFAOYSA-N 0.000 description 3
- CNSRBJWFPJMRFB-UHFFFAOYSA-N 2,8-diphenyl-4-[4-(9-phenylfluoren-9-yl)phenyl]dibenzothiophene Chemical compound C1=CC=CC=C1C1=CC=C(SC=2C3=CC(=CC=2C=2C=CC(=CC=2)C2(C4=CC=CC=C4C4=CC=CC=C42)C=2C=CC=CC=2)C=2C=CC=CC=2)C3=C1 CNSRBJWFPJMRFB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WAJDLGKOJABKAN-UHFFFAOYSA-N 3-(4-naphthalen-1-ylphenyl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=CC(=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 WAJDLGKOJABKAN-UHFFFAOYSA-N 0.000 description 3
- WQRYZOAFWABMBD-UHFFFAOYSA-N 3-(4-phenanthren-9-ylphenyl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=CC(=CC=3)C=3C4=CC=CC=C4C4=CC=CC=C4C=3)C=C2C2=CC=CC=C21 WQRYZOAFWABMBD-UHFFFAOYSA-N 0.000 description 3
- FHLAIKCAZNTSAN-UHFFFAOYSA-N 4-(4-phenanthren-9-ylphenyl)dibenzothiophene Chemical compound C1=CC=C2C(C3=CC=C(C=C3)C3=C4SC=5C(C4=CC=C3)=CC=CC=5)=CC3=CC=CC=C3C2=C1 FHLAIKCAZNTSAN-UHFFFAOYSA-N 0.000 description 3
- QECCOVYUCJYUJE-UHFFFAOYSA-N 4-[3-(9,10-diphenylanthracen-2-yl)phenyl]dibenzofuran Chemical compound C1=CC=CC=C1C(C1=CC=C(C=C11)C=2C=C(C=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)=C(C=CC=C2)C2=C1C1=CC=CC=C1 QECCOVYUCJYUJE-UHFFFAOYSA-N 0.000 description 3
- RXCFFTCQVUUMFK-UHFFFAOYSA-N 4-[3-(9,10-diphenylanthracen-2-yl)phenyl]dibenzothiophene Chemical compound C1=CC=CC=C1C(C1=CC=C(C=C11)C=2C=C(C=CC=2)C=2C=3SC4=CC=CC=C4C=3C=CC=2)=C(C=CC=C2)C2=C1C1=CC=CC=C1 RXCFFTCQVUUMFK-UHFFFAOYSA-N 0.000 description 3
- RVTNHUBWDWSZKX-UHFFFAOYSA-N 4-[3-[3-(9-phenylfluoren-9-yl)phenyl]phenyl]dibenzofuran Chemical compound C1=CC=CC=C1C1(C=2C=C(C=CC=2)C=2C=C(C=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C2=CC=CC=C2C2=CC=CC=C21 RVTNHUBWDWSZKX-UHFFFAOYSA-N 0.000 description 3
- OPYUBDQDQKABTN-UHFFFAOYSA-N 4-phenyl-6-[4-(9-phenylfluoren-9-yl)phenyl]dibenzothiophene Chemical compound C1=CC=CC=C1C1=CC=CC2=C1SC1=C(C=3C=CC(=CC=3)C3(C4=CC=CC=C4C4=CC=CC=C43)C=3C=CC=CC=3)C=CC=C12 OPYUBDQDQKABTN-UHFFFAOYSA-N 0.000 description 3
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-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
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 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 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 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 3
- 238000000151 deposition Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920002620 polyvinyl fluoride Polymers 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000005019 vapor deposition process Methods 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
- NFFQEUGCDMASSS-UHFFFAOYSA-N (3-dibenzofuran-4-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=3OC4=CC=CC=C4C=3C=CC=2)=C1 NFFQEUGCDMASSS-UHFFFAOYSA-N 0.000 description 2
- NLOHUARANQHPPJ-UHFFFAOYSA-N (3-dibenzothiophen-4-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=3SC4=CC=CC=C4C=3C=CC=2)=C1 NLOHUARANQHPPJ-UHFFFAOYSA-N 0.000 description 2
- IPNLBJDLLBQZDZ-UHFFFAOYSA-N 1-N,6-N-diphenyl-1-N,6-N-bis[4-(9-phenylfluoren-9-yl)phenyl]pyrene-1,6-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C1(C2=CC=CC=C2C2=CC=CC=C21)C=1C=CC=CC=1)C1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC=CC=2)C=C1 IPNLBJDLLBQZDZ-UHFFFAOYSA-N 0.000 description 2
- HDMYKJVSQIHZLM-UHFFFAOYSA-N 1-[3,5-di(pyren-1-yl)phenyl]pyrene Chemical compound C1=CC(C=2C=C(C=C(C=2)C=2C3=CC=C4C=CC=C5C=CC(C3=C54)=CC=2)C=2C3=CC=C4C=CC=C5C=CC(C3=C54)=CC=2)=C2C=CC3=CC=CC4=CC=C1C2=C43 HDMYKJVSQIHZLM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UOCMXZLNHQBBOS-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol zinc Chemical compound [Zn].Oc1ccccc1-c1nc2ccccc2o1.Oc1ccccc1-c1nc2ccccc2o1 UOCMXZLNHQBBOS-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- OZNXPZBQVNNJCS-UHFFFAOYSA-N 2-bromo-9,10-diphenylanthracene Chemical compound C=12C=CC=CC2=C(C=2C=CC=CC=2)C2=CC(Br)=CC=C2C=1C1=CC=CC=C1 OZNXPZBQVNNJCS-UHFFFAOYSA-N 0.000 description 2
- MNGHUUSEERRBBG-UHFFFAOYSA-N 3,6-di(dibenzothiophen-4-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C4=C(C5=CC=CC=C5S4)C=CC=3)C=C2C2=CC(C=3C4=C(C5=CC=CC=C5S4)C=CC=3)=CC=C21 MNGHUUSEERRBBG-UHFFFAOYSA-N 0.000 description 2
- LEXFLAWDYOIRJK-UHFFFAOYSA-N 3-(3-bromophenyl)-9-phenylcarbazole Chemical compound BrC1=CC=CC(C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)=C1 LEXFLAWDYOIRJK-UHFFFAOYSA-N 0.000 description 2
- FYQQACRHXSARMX-UHFFFAOYSA-N 3-(3-dibenzothiophen-4-ylphenyl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C(C=CC=3)C=3C4=C(C5=CC=CC=C5S4)C=CC=3)C=C2C2=CC=CC=C21 FYQQACRHXSARMX-UHFFFAOYSA-N 0.000 description 2
- ZOFZDXWPOZDHKZ-UHFFFAOYSA-N 3-(4-dibenzothiophen-4-ylphenyl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=CC(=CC=3)C=3C4=C(C5=CC=CC=C5S4)C=CC=3)C=C2C2=CC=CC=C21 ZOFZDXWPOZDHKZ-UHFFFAOYSA-N 0.000 description 2
- ULQQUIBGFOIFGD-UHFFFAOYSA-N 4-[2-(2-dibenzothiophen-4-ylphenyl)phenyl]dibenzothiophene Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC2=C1SC1=CC=CC=C12 ULQQUIBGFOIFGD-UHFFFAOYSA-N 0.000 description 2
- SMAJQIMJGFHCCR-UHFFFAOYSA-N 4-[3,5-di(dibenzothiophen-4-yl)phenyl]dibenzothiophene Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2C1=CC(C=2C=3SC4=CC=CC=C4C=3C=CC=2)=CC(C2=C3SC=4C(C3=CC=C2)=CC=CC=4)=C1 SMAJQIMJGFHCCR-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 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 2
- 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 2
- RSQXKVWKJVUZDG-UHFFFAOYSA-N 9-bromophenanthrene Chemical compound C1=CC=C2C(Br)=CC3=CC=CC=C3C2=C1 RSQXKVWKJVUZDG-UHFFFAOYSA-N 0.000 description 2
- DDCOSPFEMPUOFY-UHFFFAOYSA-N 9-phenyl-3-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 DDCOSPFEMPUOFY-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000002378 acidificating effect 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
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 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 2
- 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 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- KZPXREABEBSAQM-UHFFFAOYSA-N cyclopenta-1,3-diene;nickel(2+) Chemical compound [Ni+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KZPXREABEBSAQM-UHFFFAOYSA-N 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000001035 drying Methods 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
- 238000002474 experimental method Methods 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 239000011346 highly viscous material Substances 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- YGNUPJXMDOFFDO-UHFFFAOYSA-N n,4-diphenylaniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 YGNUPJXMDOFFDO-UHFFFAOYSA-N 0.000 description 2
- AJNJGJDDJIBTBP-UHFFFAOYSA-N n-(9,10-diphenylanthracen-2-yl)-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 AJNJGJDDJIBTBP-UHFFFAOYSA-N 0.000 description 2
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 2
- 238000001225 nuclear magnetic resonance method Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003287 optical effect Effects 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
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- LYKXFSYCKWNWEZ-UHFFFAOYSA-N pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile Chemical compound N1=CC=CC2=C(N=C(C(C#N)=N3)C#N)C3=C(C=CC=N3)C3=C21 LYKXFSYCKWNWEZ-UHFFFAOYSA-N 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
- 239000003566 sealing material Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- IXMJHMMAXNPBKP-UHFFFAOYSA-N (2,8-diphenyldibenzothiophen-4-yl)boronic acid Chemical compound C=1C=C2SC=3C(B(O)O)=CC(C=4C=CC=CC=4)=CC=3C2=CC=1C1=CC=CC=C1 IXMJHMMAXNPBKP-UHFFFAOYSA-N 0.000 description 1
- KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 description 1
- KEOLYBMGRQYQTN-UHFFFAOYSA-N (4-bromophenyl)-phenylmethanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=CC=C1 KEOLYBMGRQYQTN-UHFFFAOYSA-N 0.000 description 1
- BQHVXFQXTOIMQM-UHFFFAOYSA-N (4-naphthalen-1-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=CC=CC=C12 BQHVXFQXTOIMQM-UHFFFAOYSA-N 0.000 description 1
- CERRROIEYSGXNN-UHFFFAOYSA-N (6-phenyldibenzothiophen-4-yl)boronic acid Chemical compound C=12SC=3C(B(O)O)=CC=CC=3C2=CC=CC=1C1=CC=CC=C1 CERRROIEYSGXNN-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-UHFFFAOYSA-N 0.000 description 1
- XFDYBCQHRPMIGD-UHFFFAOYSA-N 1-N,6-N-bis(3-methylphenyl)-1-N,6-N-bis[3-(9-phenylfluoren-9-yl)phenyl]pyrene-1,6-diamine Chemical compound CC1=CC=CC(N(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC=CC=2)C=2C3=CC=C4C=CC(=C5C=CC(C3=C54)=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C=CC=2)C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC=CC=2)=C1 XFDYBCQHRPMIGD-UHFFFAOYSA-N 0.000 description 1
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UVAMFBJPMUMURT-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenethiol Chemical compound FC1=C(F)C(F)=C(S)C(F)=C1F UVAMFBJPMUMURT-UHFFFAOYSA-N 0.000 description 1
- NTOCEJPHYKUUAZ-UHFFFAOYSA-N 2,3-bis(4-fluorophenyl)pyrido[2,3-b]pyrazine Chemical compound C1=CC(F)=CC=C1C1=NC2=CC=CN=C2N=C1C1=CC=C(F)C=C1 NTOCEJPHYKUUAZ-UHFFFAOYSA-N 0.000 description 1
- RBAXWBRRSJYIIW-UHFFFAOYSA-N 2,3-diphenylpyrido[2,3-b]pyrazine Chemical compound C1=CC=CC=C1C1=NC2=CC=CN=C2N=C1C1=CC=CC=C1 RBAXWBRRSJYIIW-UHFFFAOYSA-N 0.000 description 1
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-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
- JBWRZTKHMKVFMQ-UHFFFAOYSA-N 3,6-dibromo-9-phenylcarbazole Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 JBWRZTKHMKVFMQ-UHFFFAOYSA-N 0.000 description 1
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-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
- QKVWPNRUXZYLQV-UHFFFAOYSA-N 4-(3-triphenylen-2-ylphenyl)dibenzothiophene Chemical compound C1=CC=C2C3=CC(C=4C=CC=C(C=4)C4=C5SC=6C(C5=CC=C4)=CC=CC=6)=CC=C3C3=CC=CC=C3C2=C1 QKVWPNRUXZYLQV-UHFFFAOYSA-N 0.000 description 1
- LOIBXBUXWRVJCF-UHFFFAOYSA-N 4-(4-aminophenyl)-3-phenylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=CC=C1 LOIBXBUXWRVJCF-UHFFFAOYSA-N 0.000 description 1
- KOGDFDWINXIWHI-OWOJBTEDSA-N 4-[(e)-2-(4-aminophenyl)ethenyl]aniline Chemical compound C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1 KOGDFDWINXIWHI-OWOJBTEDSA-N 0.000 description 1
- CGHRSEPUYCMSSV-UHFFFAOYSA-N 4-[4-(10-phenylanthracen-9-yl)phenyl]dibenzothiophene Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=2C=3SC4=CC=CC=C4C=3C=CC=2)C=C1 CGHRSEPUYCMSSV-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- HGHBHXZNXIDZIZ-UHFFFAOYSA-N 4-n-(9,10-diphenylanthracen-2-yl)-1-n,1-n,4-n-triphenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C2C(C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C=CC=CC=3)C2=CC=1)C1=CC=CC=C1 HGHBHXZNXIDZIZ-UHFFFAOYSA-N 0.000 description 1
- KLNDKWAYVMOOFU-UHFFFAOYSA-N 4-n-[9,10-bis(2-phenylphenyl)anthracen-2-yl]-1-n,1-n,4-n-triphenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C2C(C=3C(=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=CC=1)C1=CC=CC=C1 KLNDKWAYVMOOFU-UHFFFAOYSA-N 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
- ZCAPDAJQDNCVAE-UHFFFAOYSA-N 5,6,7,8,14,15,16,17,23,24,25,26,32,33,34,35-hexadecafluoro-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13(18),14,16,19,21(38),22(27),23,25,28,30(37),31(36),32,34-nonadecaene Chemical compound C12=C(F)C(F)=C(F)C(F)=C2C(N=C2NC(C3=C(F)C(F)=C(F)C(F)=C32)=N2)=NC1=NC([C]1C(F)=C(F)C(F)=C(F)C1=1)=NC=1N=C1[C]3C(F)=C(F)C(F)=C(F)C3=C2N1 ZCAPDAJQDNCVAE-UHFFFAOYSA-N 0.000 description 1
- GUIIZZCUSXBMJN-UHFFFAOYSA-N 5,8-bis(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctylcarbamoyl)naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC(C(O)=NCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=NCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F GUIIZZCUSXBMJN-UHFFFAOYSA-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
- MWQDBYKWEGXSJW-UHFFFAOYSA-N 6,12-dimethoxy-5,11-diphenylchrysene Chemical compound C12=C3C=CC=CC3=C(OC)C(C=3C=CC=CC=3)=C2C2=CC=CC=C2C(OC)=C1C1=CC=CC=C1 MWQDBYKWEGXSJW-UHFFFAOYSA-N 0.000 description 1
- XQNMSKCVXVXEJT-UHFFFAOYSA-N 7,14,25,32-tetrazaundecacyclo[21.13.2.22,5.03,19.04,16.06,14.08,13.020,37.024,32.026,31.034,38]tetraconta-1(36),2,4,6,8,10,12,16,18,20(37),21,23(38),24,26,28,30,34,39-octadecaene-15,33-dione 7,14,25,32-tetrazaundecacyclo[21.13.2.22,5.03,19.04,16.06,14.08,13.020,37.025,33.026,31.034,38]tetraconta-1(37),2,4,6,8,10,12,16,18,20,22,26,28,30,32,34(38),35,39-octadecaene-15,24-dione Chemical compound O=c1c2ccc3c4ccc5c6nc7ccccc7n6c(=O)c6ccc(c7ccc(c8nc9ccccc9n18)c2c37)c4c56.O=c1c2ccc3c4ccc5c6c(ccc(c7ccc(c8nc9ccccc9n18)c2c37)c46)c1nc2ccccc2n1c5=O XQNMSKCVXVXEJT-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
- RGEOJBAJNJQRPF-UHFFFAOYSA-N 9,10-bis(hexylcarbamoyl)perylene-3,4-dicarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(=O)NCCCCCC)C2=C1C3=CC=C2C(=O)NCCCCCC RGEOJBAJNJQRPF-UHFFFAOYSA-N 0.000 description 1
- ULYOATJQTYIRQV-UHFFFAOYSA-N 9,10-bis(octylcarbamoyl)perylene-3,4-dicarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(=O)NCCCCCCCC)C2=C1C3=CC=C2C(=O)NCCCCCCCC ULYOATJQTYIRQV-UHFFFAOYSA-N 0.000 description 1
- LWBYEDXZPBXTFL-UHFFFAOYSA-N 9-(3-bromophenyl)-9-phenylfluorene Chemical compound BrC1=CC=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC=CC=2)=C1 LWBYEDXZPBXTFL-UHFFFAOYSA-N 0.000 description 1
- JZAFCDUOMYNXTO-UHFFFAOYSA-N 9-(4-bromophenyl)phenanthrene Chemical compound C1=CC(Br)=CC=C1C1=CC2=CC=CC=C2C2=CC=CC=C12 JZAFCDUOMYNXTO-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
- DTGCMKMICLCAQU-UHFFFAOYSA-N 9-[3-[2-(3-phenanthren-9-ylphenyl)ethenyl]phenyl]phenanthrene Chemical compound C1=CC=C2C(C=3C=CC=C(C=3)C=CC=3C=C(C=CC=3)C=3C4=CC=CC=C4C4=CC=CC=C4C=3)=CC3=CC=CC=C3C2=C1 DTGCMKMICLCAQU-UHFFFAOYSA-N 0.000 description 1
- UQVFZEYHQJJGPD-UHFFFAOYSA-N 9-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 UQVFZEYHQJJGPD-UHFFFAOYSA-N 0.000 description 1
- HOGUGXVETSOMRE-UHFFFAOYSA-N 9-[4-[2-(4-phenanthren-9-ylphenyl)ethenyl]phenyl]phenanthrene Chemical compound C1=CC=C2C(C3=CC=C(C=C3)C=CC=3C=CC(=CC=3)C=3C4=CC=CC=C4C4=CC=CC=C4C=3)=CC3=CC=CC=C3C2=C1 HOGUGXVETSOMRE-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
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 229910018125 Al-Si Inorganic materials 0.000 description 1
- 229910018520 Al—Si Inorganic materials 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- CFZRUXMJHALVPF-UHFFFAOYSA-N [4-(9-phenylcarbazol-3-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 CFZRUXMJHALVPF-UHFFFAOYSA-N 0.000 description 1
- GBKYFASVJPZWLI-UHFFFAOYSA-N [Pt+2].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 Chemical compound [Pt+2].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 GBKYFASVJPZWLI-UHFFFAOYSA-N 0.000 description 1
- SUFKFXIFMLKZTD-UHFFFAOYSA-N [Tb+3].N1=CC=CC2=CC=C3C=CC=NC3=C12 Chemical compound [Tb+3].N1=CC=CC2=CC=C3C=CC=NC3=C12 SUFKFXIFMLKZTD-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
- 230000009471 action Effects 0.000 description 1
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 230000002457 bidirectional effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- LNDJVIYUJOJFSO-UHFFFAOYSA-N cyanoacetylene Chemical group C#CC#N LNDJVIYUJOJFSO-UHFFFAOYSA-N 0.000 description 1
- BHMABKBIKLSYGX-UHFFFAOYSA-N cyclopenta-1,3-diene 5-methylcyclopenta-1,3-diene nickel(2+) Chemical compound [Ni++].c1cc[cH-]c1.C[c-]1cccc1 BHMABKBIKLSYGX-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 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
- 230000005484 gravity Effects 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000011261 inert gas 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
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 1
- BBNZOXKLBAWRSH-UHFFFAOYSA-N n,9-diphenyl-n-[4-(10-phenylanthracen-9-yl)phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 BBNZOXKLBAWRSH-UHFFFAOYSA-N 0.000 description 1
- LNFOMBWFZZDRKO-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(10-phenylanthracen-9-yl)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 LNFOMBWFZZDRKO-UHFFFAOYSA-N 0.000 description 1
- XAWQWMLNBYNXJX-UHFFFAOYSA-N n,n-diphenyl-9-[4-(10-phenylanthracen-9-yl)phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC(=CC=3)C=3C4=CC=CC=C4C(C=4C=CC=CC=4)=C4C=CC=CC4=3)C2=CC=1)C1=CC=CC=C1 XAWQWMLNBYNXJX-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
- FPOBXNYAWLLCGZ-UHFFFAOYSA-N nickel(2+);1,2,3,4,5-pentamethylcyclopenta-1,3-diene Chemical compound [Ni+2].CC=1C(C)=C(C)[C-](C)C=1C.CC=1C(C)=C(C)[C-](C)C=1C FPOBXNYAWLLCGZ-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NGSMDHYQABJENH-UHFFFAOYSA-N oxovanadium(2+) 6,15,24,33-tetraphenoxy-2,11,20,29,37,39-hexaza-38,40-diazanidanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13(18),14,16,19(39),20,22(27),23,25,28,30(37),31(36),32,34-nonadecaene Chemical compound [V+2]=O.C=1C=C2C(N=C3[N-]C(C4=CC=C(OC=5C=CC=CC=5)C=C43)=NC3=NC(C4=CC=C(OC=5C=CC=CC=5)C=C43)=NC=3[N-]C(=C4C=CC(OC=5C=CC=CC=5)=CC4=3)N=3)=NC=3C2=CC=1OC1=CC=CC=C1 NGSMDHYQABJENH-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- AZVQGIPHTOBHAF-UHFFFAOYSA-N perfluoropentacene Chemical compound FC1=C(F)C(F)=C(F)C2=C(F)C3=C(F)C4=C(F)C5=C(F)C(F)=C(F)C(F)=C5C(F)=C4C(F)=C3C(F)=C21 AZVQGIPHTOBHAF-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000007639 printing Methods 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
- 238000011158 quantitative evaluation Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 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
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 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
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 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
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- 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
- 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
- H10K50/13—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 comprising stacked EL layers within one EL unit
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
-
- 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]
- H10K50/14—Carrier transporting layers
Abstract
【解決手段】ジベンゾチオフェン骨格又はジベンゾフラン骨格を有する複素環化合物と、該複素環化合物に対して電子受容性を示す無機化合物とを含む複合材料を提供する。また、一対の電極間に発光物質を含む層を有し、該発光物質を含む層は、該複合材料を含む層を有する発光素子を提供する。
【選択図】図1
Description
本実施の形態では、本発明の一態様の複合材料について説明する。
本実施の形態では、本発明の一態様の発光素子について図1を用いて説明する。
本実施の形態では、本発明の一態様の、発光素子を有する発光装置について図3を用いて説明する。なお、図3(A)は、発光装置を示す上面図、図3(B)は図3(A)をA−B及びC−Dで切断した断面図である。
本実施の形態では、本発明を適用した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5、図6を用いて説明する。
まず、ガラス基板を真空蒸着装置内の基板ホルダーに固定する。そして、4−[4−(9−フェニル−9H−フルオレン−9−イル)フェニル]−6−フェニルジベンゾチオフェン(略称:DBTFLP−IV)と酸化モリブデン(VI)とをそれぞれ別の抵抗加熱式の蒸発源に入れ、真空に引いた状態で、共蒸着法によりDBTFLP−IVと酸化モリブデンとを含む膜を形成した。この時、DBTFLP−IVと酸化モリブデン(VI)の比率が質量比で4:2(=DBTFLP−IV:酸化モリブデン)、4:1、4:0.5となるようにそれぞれ共蒸着した。なお、膜厚は50nmとした。
まず、ガラス基板1100上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、陽極として機能する第1の電極1101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の正孔注入層1111は、9−フェニル−3−[4−(10−フェニル−9−アントリル)フェニル]−9H−カルバゾール(略称:PCzPA)及び酸化モリブデン(VI)を共蒸着することで形成した。その膜厚は、50nmとし、PCzPAと酸化モリブデン(VI)の比率は、質量比で4:2(=PCzPA:酸化モリブデン)となるように調節した。正孔注入層1111以外は、発光素子1と同様に作製した。
比較発光素子3の正孔注入層1111は、4−フェニル−4’−(9−フェニルフルオレン−9−イル)トリフェニルアミン(略称:BPAFLP)及び酸化モリブデン(VI)を共蒸着することで形成した。その膜厚は、50nmとし、BPAFLPと酸化モリブデン(VI)の比率は、質量比で4:2(=BPAFLP:酸化モリブデン)となるように調節した。正孔注入層1111以外は、発光素子1と同様に作製した。
発光素子4の正孔注入層1111は、1,3,5−トリ(ジベンゾチオフェン−4−イル)−ベンゼン(略称:DBT3P−II)及び酸化モリブデン(VI)を共蒸着することで形成した。その膜厚は、50nmとし、DBT3P−IIと酸化モリブデン(VI)の比率は、質量比で4:2(=DBT3P−II:酸化モリブデン)となるように調節した。正孔注入層1111以外は、実施例2に示した発光素子1と同様に作製した。
発光素子5の正孔注入層1111は、2,8−ジフェニル−4−[4−(9−フェニル−9H−フルオレン−9−イル)フェニル]ジベンゾチオフェン(略称:DBTFLP−III)及び酸化モリブデン(VI)を共蒸着することで形成した。その膜厚は、50nmとし、DBTFLP−IIIと酸化モリブデン(VI)の比率は、質量比で4:2(=DBTFLP−III:酸化モリブデン)となるように調節した。正孔注入層1111以外は、実施例2に示した発光素子1と同様に作製した。
まず、ガラス基板を真空蒸着装置内の基板ホルダーに固定する。そして、3−〔4−(ジベンゾチオフェン−4−イル)−フェニル〕−9−フェニル−9H−カルバゾール(略称:DBTPPC−II)と酸化モリブデン(VI)とをそれぞれ別の抵抗加熱式の蒸発源に入れ、真空に引いた状態で、共蒸着法によりDBTPPC−IIと酸化モリブデンとを含む膜を形成した。この時、DBTPPC−IIと酸化モリブデン(VI)の比率が質量比で4:2(=DBTPPC−II:酸化モリブデン)、4:1、4:0.5となるようにそれぞれ共蒸着した。なお、膜厚は50nmとした。
まず、実施例2に示した発光素子1と同様に、ガラス基板1100上にITSOを成膜することで、第1の電極1101を形成した。
発光素子7の正孔注入層1111は、4−{3−[3−(9−フェニル−9H−フルオレン−9−イル)フェニル]−フェニル}ジベンゾフラン(略称:mmDBFFLBi−II)及び酸化モリブデン(VI)を共蒸着することで形成した。その膜厚は、50nmとし、mmDBFFLBi−IIと酸化モリブデン(VI)の比率は、質量比で4:2(=mmDBFFLBi−II:酸化モリブデン)となるように調節した。
発光素子8の正孔注入層1111は、mmDBFFLBi−II及び酸化モリブデン(VI)を共蒸着することで形成した。その膜厚は、50nmとし、mmDBFFLBi−IIと酸化モリブデン(VI)の比率は、質量比で4:2(=mmDBFFLBi−II:酸化モリブデン)となるように調節した。
まず、ガラス基板1100上に、ITSO膜をスパッタリング法にて成膜し、陽極として機能する第1の電極1101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10の第1の正孔注入層1111aは、PCzPA及び酸化モリブデン(VI)を共蒸着することで形成した。その膜厚は、50nmとし、PCzPAと酸化モリブデン(VI)の比率は、質量比で4:2(=PCzPA:酸化モリブデン)となるように調節した。
まず、NPBと酸化モリブデンとを含む従来の複合材料に関して、吸収スペクトルを測定し、DBT3P−IIと酸化モリブデンとを含む本発明の一態様の複合材料(図8)と比較した。
本実施例の試料1乃至6、及び比較試料1乃至13について説明する。
測定は、電子スピン共鳴測定装置 JES−FA200(日本電子製)を使用し、共振周波数約9.4GHz、変調周波数100kHz、変調幅0.6mT、時定数0.1sec、掃引時間4min、測定温度は室温、の条件で行った。そして、Mn2+第3及び第4シグナルの位置により磁場補正を行った。測定により得られる電子スピン共鳴(ESR)スペクトルの強度は、不対電子の数を反映しており、その強度を比較することにより有機化合物と酸化モリブデンの間における電荷移動相互作用の生じやすさを間接的に把握することができる。なお、ESRスペクトルのピークから算出されたg値は、2.001〜2.006の範囲であり、自由電子のg値(2.0023)近傍の数値を示していた。
図41に、試料6及び比較試料11のESRスペクトルを示す。図41において、横軸は磁場(単位:mT)を、縦軸は強度を表す。
以上で得られたESRスペクトルの強度、ピークの対称性、及びg値から、以下のように考察を行った。
上記実施例で用いた4−[4−(9−フェニル−9H−フルオレン−9−イル)フェニル]−6−フェニルジベンゾチオフェン(略称:DBTFLP−IV)の合成方法について説明する。DBTFLP−IVの構造を以下に示す。
1H NMR(CDCl3,300MHz):7.16−7.59(m,22H),7.69−7.71(m,2H),7.79(d,J=7.5Hz,2H),8.14−8.18(m,2H)。
上記実施例で用いた4,4’−(ビフェニル−2,2’−ジイル)−ビス−ジベンゾチオフェン(略称:oDBTBP−II)の合成方法について説明する。oDBTBP−IIの構造を以下に示す。
上記実施例で用いた2,8−ジフェニル−4−[4−(9−フェニル−9H−フルオレン−9−イル)フェニル]ジベンゾチオフェン(略称:DBTFLP−III)の合成方法について説明する。DBTFLP−IIIの構造を以下に示す。
1H NMR(CDCl3,300MHz):7.23−7.52(m,20H),7.65−7.76(m,8H),7.81(d,J=6.9Hz,1H),7.88(d,J=8.1Hz,1H),8.40(dd,J=11.7Hz,1.5Hz,2H)。
上記実施例で用いた3,6−ジ−(ジベンゾチオフェン−4−イル)−9−フェニル−9H−カルバゾール(略称:DBT2PC−II)の合成方法について説明する。DBT2PC−IIの構造を以下に示す。
1H NMR(CDCl3,300MHz):δ(ppm)=7.44−7.70(m、15H)、7.82−7.86(m、4H)、8.15−8.22(m、4H)、8.57(d、J=1.5Hz、2H)
上記実施例で用いた4−[3−(9,10−ジフェニル−2−アントリル)フェニル]ジベンゾチオフェン(略称:2mDBTPPA−II)の合成方法について説明する。2mDBTPPA−IIの構造を以下に示す。
1H NMR(CDCl3,300MHz):δ=7.33(q,J1=3.3Hz,2H),7.46−7.73(m,20H),7.80−7.87(m,2H),7.99(st,J1=1.8Hz,1H),8.03(sd,J1=1.5Hz,1H),8.14−8.20(m,2H)
上記実施例で用いた4−[3−(9,10−ジフェニル−2−アントリル)フェニル]ジベンゾフラン(略称:2mDBFPPA−II)の合成方法について説明する。2mDBFPPA−IIの構造を以下に示す。
1H NMR(CDCl3,300MHz):δ=7.31−7.67(m,19H),7.69−7.73(m,3H),7.80−7.86(m,2H),7.95(dd,J1=0.90Hz,J2=1.8Hz,1H),7.98−8.01(m,2H),8.07(s,1H)
上記実施例で用いた4−フェニル−4’−(9−フェニルフルオレン−9−イル)トリフェニルアミン(略称:BPAFLP)の合成方法について具体的に説明する。BPAFLPの構造を以下に示す。
100mL三口フラスコにて、マグネシウムを1.2g(50mmol)減圧下で30分加熱撹拌し、マグネシウムを活性化させた。これを室温にまで冷まして窒素雰囲気にした後、ジブロモエタン数滴を加えて発泡、発熱するのを確認した。ここにジエチルエーテル10mL中に溶かした2−ブロモビフェニルを12g(50mmol)ゆっくり滴下した後、2.5時間加熱還流撹拌してグリニヤール試薬とした。
100mL三口フラスコへ、9−(4−ブロモフェニル)−9−フェニルフルオレンを3.2g(8.0mmol)、4−フェニル−ジフェニルアミンを2.0g(8.0mmol)、ナトリウム tert−ブトキシドを1.0g(10mmol)、ビス(ジベンジリデンアセトン)パラジウム(0)を23mg(0.04mmol)加え、フラスコ内の雰囲気を窒素置換した。この混合物へ、脱水キシレン20mLを加えた。この混合物を、減圧下で攪拌しながら脱気した後、トリ(tert−ブチル)ホスフィン(10wt%ヘキサン溶液)0.2mL(0.1mmol)を加えた。この混合物を、窒素雰囲気下、110℃で2時間加熱撹拌し、反応させた。
上記実施例で用いたN,N’−ビス〔4−(9−フェニル−9H−フルオレン−9−イル)フェニル〕−N,N’−ジフェニルピレン−1,6−ジアミン(略称:1,6FLPAPrn)の合成方法について具体的に説明する。1,6FLPAPrnの構造を以下に示す。
1H NMR(CDCl3,300MHz):δ=6.88−6.91(m,6H),7.00−7.03(m,8H),7.13−7.40(m,26H),7.73−7.80(m,6H),7.87(d,J=9.0Hz,2H),8.06−8.09(m,4H)
上記実施例で用いた3−[4−(9−フェナントリル)−フェニル]−9−フェニル−9H−カルバゾール(略称:PCPPn)の合成方法について具体的に説明する。PCPPnの構造を以下に示す。
300mL三口フラスコに、3−(4−ブロモフェニル)−9−フェニル−9H−カルバゾールを8.0g(20mmol)入れ、フラスコ内の雰囲気を窒素置換したのち、脱水テトラヒドロフラン(略称:THF)100mLを加えて−78℃にした。この混合液に1.65mol/Lのn−ブチルリチウムヘキサン溶液15mL(24mmol)を滴下し、2時間撹拌した。この混合物にホウ酸トリメチル3.4mL(30mmol)を加え、−78℃で2時間、室温で18時間撹拌した。反応後、この反応溶液に1M希塩酸を酸性になるまで加えて7時間撹拌した。これを酢酸エチルで抽出し、得られた有機層を飽和食塩水で洗浄した。洗浄後、有機層に硫酸マグネシウムを加えて水分を吸着させた。この懸濁液を濾過し、得られた濾液を濃縮し、ヘキサンを加え超音波をかけたのち、再結晶したところ、目的の白色粉末を収量6.4g、収率88%で得た。上記ステップ1の反応スキームを下記(I−1)に示す。
200mL三口フラスコへ9−フェニル−9H−カルバゾール−3−イル−フェニル−4−ボロン酸を1.5g(5.0mmol)、9−ブロモフェナントレンを3.2g(11mmol)、酢酸パラジウム(II)を11mg(0.1mmol)、トリ(オルト−トリル)ホスフィンを30mg(0.1mmol)、トルエン30mL、エタノール3mL、2mol/L炭酸カリウム水溶液5mLの混合物を、減圧下で攪拌しながら脱気した後、窒素雰囲気下、90℃で6時間加熱撹拌し、反応させた。
1H NMR(CDCl3,300MHz):δ(ppm)=7.30−7.35(m,11H),7.43−7.78(m,16H),7.86−7.93(m,3H),8.01(dd,J=0.9Hz,7.8Hz,1H),8.23(d,J=7.8Hz,1H),8.47(d,J=1.5Hz,1H),8.74(d,J=8.1Hz,1H),8.80(d,J=7.8Hz,1H)。
上記実施例で用いた3−〔4−(ジベンゾチオフェン−4−イル)−フェニル〕−9−フェニル−9H−カルバゾール(略称:DBTPPC−II)の合成方法について具体的に説明する。DBTPPC−IIの構造を以下に示す。
上記実施例で用いた3−〔3−(ジベンゾチオフェン−4−イル)−フェニル〕−9−フェニル−9H−カルバゾール(略称:mDBTPPC−II)の合成方法について具体的に説明する。mDBTPPC−IIの構造を以下に示す。
上記実施例で用いた4−[4−(9−フェナントリル)フェニル]ジベンゾチオフェン(略称:DBTPPn−II)の合成方法について具体的に説明する。DBTPPn−IIの構造を以下に示す。
1H NMR(CDCl3,300MHz):δ(ppm)=7.46−7.53(m,2H),7.58−7.73(m,8H),7.80(s,1H),7.87−7.96(m,4H),8.07(d,J=8.1Hz,1H),8.18−8.24(m,2H),8.76(d,J=8.1Hz,1H),8.82(d,J=7.8Hz,1H)。
上記実施例で用いた4,4’−{(1,1’:2’,1’’:2’’,1’’’)−クアテルフェニル−3,3’’’−イル}−ビスジベンゾチオフェン(略称:mZ−DBT2−II)の合成方法について説明する。
1H NMR(CDCl3,300MHz):δ(ppm)=6.73(td,J=0.98Hz,1.95Hz,7.4Hz,2H)、7.01−7.06(m,4H)7.34−7.39(m,4H)、7.41−7.47(m,11H)、7.53−7.59(m,3H)7.69−7.72(m,2H)7.98(dd,J=1.5Hz,6.8Hz,2H)、8.08−8.11(m,2H)。
上記実施例で用いた4−{3−[3−(9−フェニル−9H−フルオレン−9−イル)フェニル]フェニル}ジベンゾフラン(略称:mmDBFFLBi−II)の合成方法について説明する。
1H NMR(CDCl3、300MHz):δ(ppm)=7.18−7.60(m,22H)、7.78(d,J=6.4Hz,2H)、7.85(td,J=1.5Hz,7.3Hz,1H)、7.96(dd,J=1.47Hz,7.81Hz,1H)、7.99−8.00(m,2H)。
上記実施例で用いた3−[4−(1−ナフチル)−フェニル]−9−フェニル−9H−カルバゾール(略称:PCPN)を製造する合成例を示す。
1H NMR(CDCl3,300MHz):δ(ppm)=7.30−7.35(m,1H),7.44−7.67(m,14H),7.76(dd,J=8.7Hz,1.8Hz,1H),7.84−7.95(m,4H),8.04(d,J=7.8,1H),8.23(d,J=7.8,1H),8.46(d,J=1.5,1H)。
101 第1の電極
102 EL層
108 第2の電極
401 ソース側駆動回路
402 画素部
403 ゲート側駆動回路
404 封止基板
405 シール材
407 空間
408 配線
409 FPC(フレキシブルプリントサーキット)
410 素子基板
411 スイッチング用TFT
412 電流制御用TFT
413 第1の電極
414 絶縁物
416 EL層
417 第2の電極
418 発光素子
423 nチャネル型TFT
424 pチャネル型TFT
501 基板
502 第1の電極
503 第2の電極
504 EL層
505 絶縁層
506 隔壁層
701 正孔注入層
702 正孔輸送層
703 発光層
704 電子輸送層
705 電子注入層
706 電子注入バッファー層
707 電子リレー層
708 複合材料層
800 EL層
801 EL層
802 EL層
803 電荷発生層
811 照明装置
812 照明装置
813 卓上照明器具
1100 基板
1101 第1の電極
1103 第2の電極
1111 正孔注入層
1111a 第1の正孔注入層
1111b 第2の正孔注入層
1112 正孔輸送層
1112a 第1の正孔輸送層
1112b 第2の正孔輸送層
1113 発光層
1113a 第1の発光層
1113b 第2の発光層
1114a 第1の電子輸送層
1114b 第2の電子輸送層
1115 電子注入層
1115a 第1の電子注入層
1115b 第2の電子注入層
1116 電子リレー層
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 ポインティングデバイス
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 (22)
- ジベンゾチオフェン骨格又はジベンゾフラン骨格を有する複素環化合物と、前記複素環化合物に対して電子受容性を示す無機化合物とを含む複合材料。
- ジベンゾチオフェン骨格又はジベンゾフラン骨格の4位に炭素数6以上70以下の置換基が結合した複素環化合物と、前記複素環化合物に対して電子受容性を示す無機化合物とを含む複合材料。
- ジベンゾチオフェン骨格又はジベンゾフラン骨格の4位にフェニル基が結合し、前記フェニル基が1以上の置換基を有し、前記フェニル基及び前記1以上の置換基の炭素数の総和が12以上70以下である複素環化合物と、前記複素環化合物に対して電子受容性を示す無機化合物とを含む複合材料。
- 請求項2又は請求項3において、
前記置換基が有する環は、それぞれ独立に、ベンゼン環、ナフタレン環、フェナントレン環、トリフェニレン環、フルオレン環、ジベンゾチオフェン環、ジベンゾフラン環から選ばれる一種又は複数種である複合材料。 - 一般式(G1)で表される複素環化合物と、前記複素環化合物に対して電子受容性を示す無機化合物とを含む複合材料。
(式中、Aは酸素又は硫黄を表し、R1〜R7は、それぞれ独立に、水素、炭素数1〜4のアルキル基、又は環を構成する炭素数が6〜25のアリール基を表し、R8〜R12は、それぞれ独立に、水素、置換もしくは無置換のフェニル基、置換もしくは無置換のナフチル基、置換もしくは無置換のフェナントリル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のジベンゾチオフェニル基、又は置換もしくは無置換のジベンゾフラニル基を表す。ただし、R8〜R12のうち、少なくとも1つは、置換もしくは無置換のフェニル基、置換もしくは無置換のナフチル基、置換もしくは無置換のフェナントリル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のジベンゾチオフェニル基、又は置換もしくは無置換のジベンゾフラニル基を表す。) - 一般式(G1)で表される複素環化合物と、前記複素環化合物に対して電子受容性を示す無機化合物とを含む複合材料。
(式中、Aは酸素又は硫黄を表し、R1〜R7は、それぞれ独立に、水素、炭素数1〜4のアルキル基、又は環を構成する炭素数が6〜25のアリール基を表し、R8〜R12は、それぞれ独立に、水素、置換もしくは無置換のフェニル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のジベンゾチオフェニル基、又は置換もしくは無置換のジベンゾフラニル基を表す。ただし、R8〜R12のうち、少なくとも1つは、置換もしくは無置換のフェニル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のジベンゾチオフェニル基、又は置換もしくは無置換のジベンゾフラニル基を表す。) - ジベンゾチオフェン骨格又はジベンゾフラン骨格を有する複素環化合物と、遷移金属酸化物とを含む複合材料。
- ジベンゾチオフェン骨格又はジベンゾフラン骨格の4位に炭素数6以上70以下の置換基が結合した複素環化合物と、遷移金属酸化物とを含む複合材料。
- ジベンゾチオフェン骨格又はジベンゾフラン骨格の4位にフェニル基が結合し、前記フェニル基が1以上の置換基を有し、前記フェニル基及び前記1以上の置換基の炭素数の総和が12以上70以下である複素環化合物と、遷移金属酸化物とを含む複合材料。
- 請求項8又は請求項9において、
前記置換基が有する環は、それぞれ独立に、ベンゼン環、ナフタレン環、フェナントレン環、トリフェニレン環、フルオレン環、ジベンゾチオフェン環、ジベンゾフラン環から選ばれる一種又は複数種である複合材料。 - 一般式(G1)で表される複素環化合物と、遷移金属酸化物とを含む複合材料。
(式中、Aは酸素又は硫黄を表し、R1〜R7は、それぞれ独立に、水素、炭素数1〜4のアルキル基、又は環を構成する炭素数が6〜25のアリール基を表し、R8〜R12は、それぞれ独立に、水素、置換もしくは無置換のフェニル基、置換もしくは無置換のナフチル基、置換もしくは無置換のフェナントリル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のジベンゾチオフェニル基、又は置換もしくは無置換のジベンゾフラニル基を表す。ただし、R8〜R12のうち、少なくとも1つは、置換もしくは無置換のフェニル基、置換もしくは無置換のナフチル基、置換もしくは無置換のフェナントリル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のジベンゾチオフェニル基、又は置換もしくは無置換のジベンゾフラニル基を表す。) - 一般式(G1)で表される複素環化合物と、遷移金属酸化物とを含む複合材料。
(式中、Aは酸素又は硫黄を表し、R1〜R7は、それぞれ独立に、水素、炭素数1〜4のアルキル基、又は環を構成する炭素数が6〜25のアリール基を表し、R8〜R12は、それぞれ独立に、水素、置換もしくは無置換のフェニル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のジベンゾチオフェニル基、又は置換もしくは無置換のジベンゾフラニル基を表す。ただし、R8〜R12のうち、少なくとも1つは、置換もしくは無置換のフェニル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のジベンゾチオフェニル基、又は置換もしくは無置換のジベンゾフラニル基を表す。) - 請求項7乃至請求項12のいずれか一項において、
前記遷移金属酸化物は、チタン酸化物、バナジウム酸化物、タンタル酸化物、モリブデン酸化物、タングステン酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、銀酸化物から選ばれる一種又は複数種である複合材料。 - 請求項1乃至請求項13のいずれか一項において、
前記複素環化合物の最高被占有軌道準位は、光電子分光法での測定値が−5.7eV以下である複合材料。 - 一対の電極間に発光物質を含む層を有し、
前記発光物質を含む層は、請求項1乃至請求項14のいずれか一項に記載の複合材料を含む層を有する発光素子。 - 請求項15において、
前記複合材料を含む層が、前記一対の電極のうち陽極として機能する電極と接する発光素子。 - 請求項15において、
前記複合材料を含む層が、前記一対の電極のうち陰極として機能する電極と接する発光素子。 - 請求項15において、
前記複合材料を含む層を2層有し、一方の層は、前記一対の電極のうち陽極として機能する電極と接し、他方の層は、前記一対の電極のうち陰極として機能する電極と接する発光素子。 - 一対の電極間に発光物質を含む層を複数有し、
複数の前記発光物質を含む層の間に、請求項1乃至請求項14のいずれか一項に記載の複合材料を含む層を有する発光素子。 - 請求項15乃至請求項19のいずれか一項に記載の発光素子を有する発光装置。
- 請求項20に記載の発光装置を表示部に有する電子機器。
- 請求項20に記載の発光装置を発光部に有する照明装置。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2011219738A JP2013012698A (ja) | 2010-10-04 | 2011-10-04 | 複合材料、発光素子、発光装置、電子機器、及び照明装置 |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010225037 | 2010-10-04 | ||
JP2010225037 | 2010-10-04 | ||
JP2011122827 | 2011-05-31 | ||
JP2011122827 | 2011-05-31 | ||
JP2011219738A JP2013012698A (ja) | 2010-10-04 | 2011-10-04 | 複合材料、発光素子、発光装置、電子機器、及び照明装置 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015005588A Division JP5969063B2 (ja) | 2010-10-04 | 2015-01-15 | 複合材料、発光素子、発光装置、電子機器、及び照明装置 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013012698A true JP2013012698A (ja) | 2013-01-17 |
JP2013012698A5 JP2013012698A5 (ja) | 2014-09-18 |
Family
ID=45889032
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011219738A Withdrawn JP2013012698A (ja) | 2010-10-04 | 2011-10-04 | 複合材料、発光素子、発光装置、電子機器、及び照明装置 |
JP2015005588A Expired - Fee Related JP5969063B2 (ja) | 2010-10-04 | 2015-01-15 | 複合材料、発光素子、発光装置、電子機器、及び照明装置 |
JP2016133870A Active JP6220424B2 (ja) | 2010-10-04 | 2016-07-06 | 複合材料、発光素子、発光装置、電子機器、及び照明装置 |
JP2017189793A Active JP6608895B2 (ja) | 2010-10-04 | 2017-09-29 | 複合材料、発光素子、発光装置、電子機器、及び照明装置 |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015005588A Expired - Fee Related JP5969063B2 (ja) | 2010-10-04 | 2015-01-15 | 複合材料、発光素子、発光装置、電子機器、及び照明装置 |
JP2016133870A Active JP6220424B2 (ja) | 2010-10-04 | 2016-07-06 | 複合材料、発光素子、発光装置、電子機器、及び照明装置 |
JP2017189793A Active JP6608895B2 (ja) | 2010-10-04 | 2017-09-29 | 複合材料、発光素子、発光装置、電子機器、及び照明装置 |
Country Status (7)
Country | Link |
---|---|
US (3) | US9496505B2 (ja) |
JP (4) | JP2013012698A (ja) |
KR (1) | KR101912675B1 (ja) |
CN (2) | CN104934535B (ja) |
DE (1) | DE112011103341B4 (ja) |
TW (1) | TWI565701B (ja) |
WO (1) | WO2012046560A1 (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013060411A (ja) * | 2010-10-15 | 2013-04-04 | Semiconductor Energy Lab Co Ltd | カルバゾール化合物、発光素子用材料、有機半導体材料、発光素子 |
JP2017168420A (ja) * | 2015-09-01 | 2017-09-21 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器及び照明装置 |
JP2018524280A (ja) * | 2015-05-18 | 2018-08-30 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
WO2018211377A1 (ja) * | 2017-05-19 | 2018-11-22 | 株式会社半導体エネルギー研究所 | 電子デバイス、発光装置、電子機器、および照明装置 |
JP2022037010A (ja) * | 2014-04-25 | 2022-03-08 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器及び照明装置 |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012033108A1 (en) | 2010-09-10 | 2012-03-15 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element and electronic device |
EP2433929B1 (en) | 2010-09-27 | 2013-10-23 | Semiconductor Energy Laboratory Co, Ltd. | Organic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device |
KR101950363B1 (ko) | 2010-10-29 | 2019-02-20 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 페난트렌 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
KR101910030B1 (ko) | 2010-11-30 | 2018-10-19 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 벤조옥사졸 유도체, 발광 소자, 발광 장치, 전자기기 및 조명 장치 |
EP2503618B1 (en) | 2011-03-23 | 2014-01-01 | Semiconductor Energy Laboratory Co., Ltd. | Composite material, light-emitting element, light-emitting device, electronic device, and lighting device |
JP6023461B2 (ja) * | 2011-05-13 | 2016-11-09 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置 |
DE102012208235B4 (de) * | 2012-05-16 | 2021-05-12 | Osram Oled Gmbh | Optoelektronisches Bauelement und Verfahren zum Herstellen eines optoelektronischen Bauelements |
KR20130136359A (ko) * | 2012-06-04 | 2013-12-12 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
WO2013183851A1 (ko) * | 2012-06-04 | 2013-12-12 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
EP2924029B1 (en) | 2013-03-15 | 2018-12-12 | Idemitsu Kosan Co., Ltd | Anthracene derivative and organic electroluminescence element using same |
KR102146105B1 (ko) * | 2013-06-13 | 2020-08-20 | 엘지디스플레이 주식회사 | 청색 인광 화합물 및 이를 사용한 유기전계발광소자 |
CN104282836B (zh) * | 2013-07-09 | 2017-04-05 | 吉林师范大学 | 掺杂Ag2O的Cs2CO3薄层结构的有机电致发光器件 |
CN103367653B (zh) * | 2013-07-10 | 2016-02-03 | 上海和辉光电有限公司 | 倒置型有机发光二极管显示器件及其制备方法 |
DE102013110037B4 (de) * | 2013-09-12 | 2018-05-09 | Osram Oled Gmbh | Verfahren zum Herstellen eines optoelektronischen Bauelementes |
CN105503518A (zh) * | 2014-10-14 | 2016-04-20 | 上海华显新材料科技有限公司 | 高纯度2-溴三亚苯的制备方法 |
CN104282840B (zh) * | 2014-10-29 | 2017-07-07 | 中国科学院长春应用化学研究所 | 一种黄色有机电致发光器件及其制备方法 |
US10644247B2 (en) | 2015-02-06 | 2020-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20230109778A (ko) * | 2015-05-29 | 2023-07-20 | 소니 세미컨덕터 솔루션즈 가부시키가이샤 | 광전변환 소자 및 고체 촬상 장치 |
KR20180095872A (ko) * | 2015-12-17 | 2018-08-28 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 전자 기기, 조명 장치, 조명 시스템, 및 유도 시스템 |
WO2017154286A1 (ja) * | 2016-03-07 | 2017-09-14 | 株式会社リコー | 素子、セル及び発電装置 |
KR20210011942A (ko) | 2018-05-17 | 2021-02-02 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 소자, 발광 장치, 전자 기기, 조명 장치, 및 전자 디바이스 |
WO2020015029A1 (zh) * | 2018-07-18 | 2020-01-23 | 北京大学深圳研究生院 | 一种半导体材料及其制备方法与应用 |
WO2020075014A1 (en) * | 2018-10-10 | 2020-04-16 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting device, light-emitting apparatus, electronic device, and lighting device |
GB2579807A (en) * | 2018-12-14 | 2020-07-08 | Sumitomo Chemical Co | Composition and organic light-emitting device |
US11903232B2 (en) | 2019-03-07 | 2024-02-13 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting device comprising charge-generation layer between light-emitting units |
CN112542553B (zh) * | 2019-09-20 | 2023-03-21 | Tcl科技集团股份有限公司 | 一种复合物及其制备方法与量子点发光二极管 |
US11482687B2 (en) | 2019-11-08 | 2022-10-25 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting device, electronic device, and lighting device |
JP7261729B2 (ja) * | 2019-12-04 | 2023-04-20 | 住友化学株式会社 | 高分子化合物及びそれを用いた発光素子 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7014A (en) * | 1850-01-15 | Folding bedstead | ||
JP2005190998A (ja) * | 2003-12-02 | 2005-07-14 | Semiconductor Energy Lab Co Ltd | 発光素子およびそれを用いた発光装置 |
JP2006074022A (ja) * | 2004-08-04 | 2006-03-16 | Semiconductor Energy Lab Co Ltd | 発光素子、表示装置及び電子機器 |
JP2007063501A (ja) * | 2005-09-02 | 2007-03-15 | Toray Ind Inc | 発光素子材料および発光素子 |
Family Cites Families (69)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2926845B2 (ja) | 1990-03-23 | 1999-07-28 | 日本電気株式会社 | 有機薄膜el素子 |
JP2824411B2 (ja) | 1995-08-25 | 1998-11-11 | 株式会社豊田中央研究所 | 有機薄膜発光素子 |
JPH10270171A (ja) | 1997-01-27 | 1998-10-09 | Junji Kido | 有機エレクトロルミネッセント素子 |
US5989737A (en) | 1997-02-27 | 1999-11-23 | Xerox Corporation | Organic electroluminescent devices |
JPH11251067A (ja) | 1998-03-02 | 1999-09-17 | Junji Kido | 有機エレクトロルミネッセント素子 |
JPH11307259A (ja) | 1998-04-23 | 1999-11-05 | Tdk Corp | 有機el素子 |
CN1293785C (zh) | 1998-06-26 | 2007-01-03 | 出光兴产株式会社 | 发光器件 |
US6172459B1 (en) | 1998-07-28 | 2001-01-09 | Eastman Kodak Company | Electron-injecting layer providing a modified interface between an organic light-emitting structure and a cathode buffer layer |
JP4255039B2 (ja) * | 1999-01-27 | 2009-04-15 | Tdk株式会社 | 有機el素子 |
TW474114B (en) | 1999-09-29 | 2002-01-21 | Junji Kido | Organic electroluminescent device, organic electroluminescent device assembly and method of controlling the emission spectrum in the device |
JP2002308837A (ja) * | 2001-04-05 | 2002-10-23 | Fuji Photo Film Co Ltd | 新規化合物、およびそれを用いた発光素子 |
US7141817B2 (en) | 2001-11-30 | 2006-11-28 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting device |
JP3933591B2 (ja) | 2002-03-26 | 2007-06-20 | 淳二 城戸 | 有機エレクトロルミネッセント素子 |
US7158161B2 (en) | 2002-09-20 | 2007-01-02 | Matsushita Electric Industrial Co., Ltd. | Organic electroluminescence element and an exposure unit and image-forming apparatus both using the element |
JP2004319136A (ja) * | 2003-04-11 | 2004-11-11 | Mitsubishi Gas Chem Co Inc | 有機el素子 |
JP4624653B2 (ja) | 2003-05-20 | 2011-02-02 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
JP2005026121A (ja) | 2003-07-03 | 2005-01-27 | Fujitsu Ltd | 有機el素子及びその製造方法並びに有機elディスプレイ |
KR20130062367A (ko) | 2003-09-26 | 2013-06-12 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광장치 |
JP4476594B2 (ja) | 2003-10-17 | 2010-06-09 | 淳二 城戸 | 有機エレクトロルミネッセント素子 |
JP4683829B2 (ja) | 2003-10-17 | 2011-05-18 | 淳二 城戸 | 有機エレクトロルミネッセント素子及びその製造方法 |
JP4243237B2 (ja) | 2003-11-10 | 2009-03-25 | 淳二 城戸 | 有機素子、有機el素子、有機太陽電池、及び、有機fet構造、並びに、有機素子の製造方法 |
JP4300176B2 (ja) | 2003-11-13 | 2009-07-22 | ローム株式会社 | 有機エレクトロルミネッセント素子 |
US7605534B2 (en) * | 2003-12-02 | 2009-10-20 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element having metal oxide and light-emitting device using the same |
KR20060110323A (ko) | 2003-12-16 | 2006-10-24 | 마츠시타 덴끼 산교 가부시키가이샤 | 유기 전기발광 소자 및 그 제조 방법 |
KR101187402B1 (ko) | 2004-05-21 | 2012-10-02 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 조명장치 |
JP4925569B2 (ja) | 2004-07-08 | 2012-04-25 | ローム株式会社 | 有機エレクトロルミネッセント素子 |
EP1624502B1 (en) | 2004-08-04 | 2015-11-18 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, display device, and electronic appliance |
US7504769B2 (en) * | 2004-12-16 | 2009-03-17 | E. I. Du Pont De Nemours + Company | Aromatic chalcogen compounds and their use |
WO2006093171A1 (en) | 2005-02-28 | 2006-09-08 | Semiconductor Energy Laboratory Co., Ltd. | Composite material, light emitting element, light emitting device and electronic appliance using the composite material |
EP1867080A4 (en) | 2005-03-23 | 2009-08-12 | Semiconductor Energy Lab | COMPOSITE MATERIAL, MATERIAL FOR A LIGHT-EMITTING ELEMENT, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING EQUIPMENT AND ELECTRONIC EQUIPMENT |
JP2006278419A (ja) * | 2005-03-28 | 2006-10-12 | Osaka Univ | 有機エレクトロルミネッセンス素子 |
CN101867019B (zh) | 2005-04-21 | 2013-01-23 | 株式会社半导体能源研究所 | 发光元件、发光器件和电子设备 |
JP5314834B2 (ja) | 2005-04-21 | 2013-10-16 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、照明装置および電子機器 |
US8007927B2 (en) | 2007-12-28 | 2011-08-30 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
US8586204B2 (en) | 2007-12-28 | 2013-11-19 | Universal Display Corporation | Phosphorescent emitters and host materials with improved stability |
JP5072271B2 (ja) * | 2005-06-22 | 2012-11-14 | 株式会社半導体エネルギー研究所 | 発光装置、及びそれを用いた電子機器 |
JP4947955B2 (ja) * | 2005-11-04 | 2012-06-06 | 三洋電機株式会社 | ジベンゾチオフェン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子 |
JP2007169581A (ja) * | 2005-11-25 | 2007-07-05 | Toray Ind Inc | 発光素子材料および発光素子 |
JP5078329B2 (ja) * | 2005-11-30 | 2012-11-21 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置並びに電子機器 |
JP5290581B2 (ja) * | 2005-12-15 | 2013-09-18 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
US7651791B2 (en) * | 2005-12-15 | 2010-01-26 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and electroluminescence device employing the same |
JP5055818B2 (ja) * | 2006-04-19 | 2012-10-24 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP2007335737A (ja) * | 2006-06-16 | 2007-12-27 | Matsushita Electric Ind Co Ltd | 有機エレクトロルミネッセント素子およびその製造方法 |
US20070290604A1 (en) * | 2006-06-16 | 2007-12-20 | Matsushita Electric Industrial Co., Ltd. | Organic electroluminescent device and method of producing the same |
JP2008112904A (ja) * | 2006-10-31 | 2008-05-15 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
TWI481089B (zh) | 2006-12-28 | 2015-04-11 | Universal Display Corp | 長使用期限之磷光性有機發光裝置結構 |
JP5326568B2 (ja) | 2007-03-07 | 2013-10-30 | 東レ株式会社 | 発光素子材料および発光素子 |
CN110724124A (zh) * | 2007-05-17 | 2020-01-24 | 株式会社半导体能源研究所 | 三唑衍生物 |
US20080314965A1 (en) | 2007-06-23 | 2008-12-25 | Roberts Mark D | System and method for authentication of engineering notebook support information |
KR20160104752A (ko) | 2007-08-08 | 2016-09-05 | 유니버셜 디스플레이 코포레이션 | 인광성 발광 다이오드의 단일 트리페닐렌 발색단 |
JP6009144B2 (ja) | 2007-08-08 | 2016-10-19 | ユニバーサル ディスプレイ コーポレイション | トリフェニレン基を含むベンゾ縮合チオフェンまたはベンゾ縮合フラン化合物 |
US20090153034A1 (en) | 2007-12-13 | 2009-06-18 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emittinig diodes |
US8221905B2 (en) | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
EP2075850A3 (en) | 2007-12-28 | 2011-08-24 | Semiconductor Energy Laboratory Co, Ltd. | Photoelectric conversion device and manufacturing method thereof |
KR20120081231A (ko) * | 2008-05-16 | 2012-07-18 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광소자, 및 조명장치 |
TWI486097B (zh) | 2008-12-01 | 2015-05-21 | Semiconductor Energy Lab | 發光元件、發光裝置、照明裝置、及電子裝置 |
JP5382426B2 (ja) | 2009-03-25 | 2014-01-08 | Nkワークス株式会社 | 注文装置 |
CN105742515A (zh) | 2009-05-29 | 2016-07-06 | 株式会社半导体能源研究所 | 发光元件、发光装置、照明装置以及电子设备 |
JP2011009205A (ja) | 2009-05-29 | 2011-01-13 | Semiconductor Energy Lab Co Ltd | 発光素子、発光装置及びその作製方法 |
CN102484923B (zh) * | 2009-09-04 | 2016-05-04 | 株式会社半导体能源研究所 | 发光元件、发光装置及其制造方法 |
US8771840B2 (en) | 2009-11-13 | 2014-07-08 | Semiconductor Energy Laboratory Co., Ltd. | Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device |
JP2011139044A (ja) | 2009-12-01 | 2011-07-14 | Semiconductor Energy Lab Co Ltd | 発光素子、発光装置、電子機器、および照明装置 |
JP2011122827A (ja) | 2009-12-08 | 2011-06-23 | Ihi Inspection & Instrumentation Co Ltd | アレイ探触子の測定方法及びその測定装置 |
EP2428512B1 (en) * | 2010-09-08 | 2014-10-22 | Semiconductor Energy Laboratory Co., Ltd. | Fluorene compound, light-emitting element, light-emitting device, electronic device and lighting device |
JP5815341B2 (ja) | 2010-09-09 | 2015-11-17 | 株式会社半導体エネルギー研究所 | 複素環化合物 |
WO2012033108A1 (en) | 2010-09-10 | 2012-03-15 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element and electronic device |
JP5623996B2 (ja) | 2010-09-21 | 2014-11-12 | 株式会社半導体エネルギー研究所 | カルバゾール誘導体 |
US9133173B2 (en) | 2010-10-15 | 2015-09-15 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole compound, material for light-emitting element, organic semiconductor material, light-emitting element |
KR101950363B1 (ko) | 2010-10-29 | 2019-02-20 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 페난트렌 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
-
2011
- 2011-09-09 DE DE112011103341.9T patent/DE112011103341B4/de active Active
- 2011-09-09 KR KR1020137011100A patent/KR101912675B1/ko active IP Right Grant
- 2011-09-09 WO PCT/JP2011/071165 patent/WO2012046560A1/en active Application Filing
- 2011-09-09 CN CN201510244010.4A patent/CN104934535B/zh active Active
- 2011-09-09 CN CN201180048041.2A patent/CN103154187B/zh not_active Expired - Fee Related
- 2011-09-23 US US13/241,694 patent/US9496505B2/en active Active
- 2011-09-26 TW TW100134615A patent/TWI565701B/zh active
- 2011-10-04 JP JP2011219738A patent/JP2013012698A/ja not_active Withdrawn
-
2015
- 2015-01-15 JP JP2015005588A patent/JP5969063B2/ja not_active Expired - Fee Related
-
2016
- 2016-07-06 JP JP2016133870A patent/JP6220424B2/ja active Active
- 2016-11-08 US US15/346,190 patent/US20170054088A1/en not_active Abandoned
-
2017
- 2017-09-29 JP JP2017189793A patent/JP6608895B2/ja active Active
-
2020
- 2020-12-30 US US17/137,620 patent/US20210151694A1/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7014A (en) * | 1850-01-15 | Folding bedstead | ||
JP2005190998A (ja) * | 2003-12-02 | 2005-07-14 | Semiconductor Energy Lab Co Ltd | 発光素子およびそれを用いた発光装置 |
JP2006074022A (ja) * | 2004-08-04 | 2006-03-16 | Semiconductor Energy Lab Co Ltd | 発光素子、表示装置及び電子機器 |
JP2007063501A (ja) * | 2005-09-02 | 2007-03-15 | Toray Ind Inc | 発光素子材料および発光素子 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013060411A (ja) * | 2010-10-15 | 2013-04-04 | Semiconductor Energy Lab Co Ltd | カルバゾール化合物、発光素子用材料、有機半導体材料、発光素子 |
JP2022037010A (ja) * | 2014-04-25 | 2022-03-08 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器及び照明装置 |
JP2018524280A (ja) * | 2015-05-18 | 2018-08-30 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
JP2017168420A (ja) * | 2015-09-01 | 2017-09-21 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器及び照明装置 |
WO2018211377A1 (ja) * | 2017-05-19 | 2018-11-22 | 株式会社半導体エネルギー研究所 | 電子デバイス、発光装置、電子機器、および照明装置 |
JPWO2018211377A1 (ja) * | 2017-05-19 | 2020-05-14 | 株式会社半導体エネルギー研究所 | 電子デバイス、発光装置、電子機器、および照明装置 |
US10950805B2 (en) | 2017-05-19 | 2021-03-16 | Semiconductor Energy Laboratory Co., Ltd. | Electronic device, light-emitting device, electronic appliance, and lighting device |
JP7257952B2 (ja) | 2017-05-19 | 2023-04-14 | 株式会社半導体エネルギー研究所 | 電子デバイス、表示装置、電子機器、及び照明装置 |
Also Published As
Publication number | Publication date |
---|---|
CN103154187B (zh) | 2015-06-17 |
JP2018006772A (ja) | 2018-01-11 |
KR20130120473A (ko) | 2013-11-04 |
WO2012046560A1 (en) | 2012-04-12 |
US20170054088A1 (en) | 2017-02-23 |
JP2016174190A (ja) | 2016-09-29 |
CN104934535A (zh) | 2015-09-23 |
US9496505B2 (en) | 2016-11-15 |
US20210151694A1 (en) | 2021-05-20 |
DE112011103341T5 (de) | 2013-07-25 |
TW201229046A (en) | 2012-07-16 |
TWI565701B (zh) | 2017-01-11 |
JP6608895B2 (ja) | 2019-11-20 |
CN103154187A (zh) | 2013-06-12 |
KR101912675B1 (ko) | 2018-10-29 |
DE112011103341B4 (de) | 2024-02-22 |
CN104934535B (zh) | 2017-09-15 |
JP6220424B2 (ja) | 2017-10-25 |
US20120080667A1 (en) | 2012-04-05 |
JP5969063B2 (ja) | 2016-08-10 |
JP2015119191A (ja) | 2015-06-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6608895B2 (ja) | 複合材料、発光素子、発光装置、電子機器、及び照明装置 | |
JP6148716B2 (ja) | 有機化合物 | |
JP7012762B2 (ja) | 発光素子、発光装置、電子機器および照明装置 | |
JP5815341B2 (ja) | 複素環化合物 | |
JP7224398B2 (ja) | 発光素子、発光装置、電子機器、照明装置、及び有機化合物 | |
JP6194089B2 (ja) | 発光素子、発光装置、電子機器、照明装置 | |
JP2012092087A (ja) | 有機化合物、発光素子、発光装置、電子機器及び照明装置 | |
JP7482270B2 (ja) | 発光素子、発光装置、電子機器、及び照明装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140801 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20140801 |
|
A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20140801 |
|
A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20140825 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140902 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141010 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20141028 |
|
A761 | Written withdrawal of application |
Free format text: JAPANESE INTERMEDIATE CODE: A761 Effective date: 20150119 |