KR101742971B1 - 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 - Google Patents
트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 Download PDFInfo
- Publication number
- KR101742971B1 KR101742971B1 KR1020167020847A KR20167020847A KR101742971B1 KR 101742971 B1 KR101742971 B1 KR 101742971B1 KR 1020167020847 A KR1020167020847 A KR 1020167020847A KR 20167020847 A KR20167020847 A KR 20167020847A KR 101742971 B1 KR101742971 B1 KR 101742971B1
- Authority
- KR
- South Korea
- Prior art keywords
- light emitting
- abbreviation
- light
- reaction
- layer
- 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.)
- Active
Links
- 125000005259 triarylamine group Chemical group 0.000 title claims abstract description 123
- 239000000126 substance Substances 0.000 title description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000006267 biphenyl group Chemical group 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000011630 iodine Substances 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 213
- 239000000463 material Substances 0.000 description 176
- 150000001875 compounds Chemical class 0.000 description 134
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 120
- 238000006243 chemical reaction Methods 0.000 description 115
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 63
- 230000015572 biosynthetic process Effects 0.000 description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- 238000003786 synthesis reaction Methods 0.000 description 63
- 239000000758 substrate Substances 0.000 description 59
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 56
- 125000003118 aryl group Chemical group 0.000 description 51
- 238000001308 synthesis method Methods 0.000 description 51
- 229910052757 nitrogen Inorganic materials 0.000 description 50
- 150000004982 aromatic amines Chemical group 0.000 description 48
- 238000000034 method Methods 0.000 description 44
- 239000000203 mixture Substances 0.000 description 43
- 239000000243 solution Substances 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000000706 filtrate Substances 0.000 description 38
- 150000001543 aryl boronic acids Chemical class 0.000 description 37
- 238000005859 coupling reaction Methods 0.000 description 36
- 239000002904 solvent Substances 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 30
- 239000002131 composite material Substances 0.000 description 29
- 239000010408 film Substances 0.000 description 29
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 238000002347 injection Methods 0.000 description 28
- 239000007924 injection Substances 0.000 description 28
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 28
- 230000002140 halogenating effect Effects 0.000 description 27
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 27
- 239000000725 suspension Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000010168 coupling process Methods 0.000 description 25
- 238000005259 measurement Methods 0.000 description 25
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 25
- 238000000862 absorption spectrum Methods 0.000 description 24
- 230000008878 coupling Effects 0.000 description 24
- -1 diphenylphosphino Chemical group 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 238000000151 deposition Methods 0.000 description 22
- 229910052751 metal Inorganic materials 0.000 description 22
- 239000002184 metal Substances 0.000 description 22
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 21
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 20
- 150000001502 aryl halides Chemical class 0.000 description 20
- 150000002894 organic compounds Chemical class 0.000 description 20
- 238000004809 thin layer chromatography Methods 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000010409 thin film Substances 0.000 description 18
- 239000002585 base Substances 0.000 description 16
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 15
- 239000010453 quartz Substances 0.000 description 15
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000000295 emission spectrum Methods 0.000 description 14
- 235000019253 formic acid Nutrition 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000003643 water by type Substances 0.000 description 14
- 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 13
- 238000006887 Ullmann reaction Methods 0.000 description 13
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 239000011159 matrix material Substances 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
- 238000007872 degassing Methods 0.000 description 11
- 230000006870 function Effects 0.000 description 11
- 239000011259 mixed solution Substances 0.000 description 11
- 239000007983 Tris buffer Substances 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- 238000005658 halogenation reaction Methods 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 230000026030 halogenation Effects 0.000 description 9
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 9
- 238000004020 luminiscence type Methods 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 9
- 238000001771 vacuum deposition Methods 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 229910044991 metal oxide Inorganic materials 0.000 description 8
- 150000004706 metal oxides Chemical class 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000007789 sealing Methods 0.000 description 8
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- 230000005281 excited state Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000004770 highest occupied molecular orbital Methods 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- 239000012046 mixed solvent Substances 0.000 description 7
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- YRPIGRRBBMFFBE-UHFFFAOYSA-N 1-(4-bromophenyl)naphthalene Chemical compound C1=CC(Br)=CC=C1C1=CC=CC2=CC=CC=C12 YRPIGRRBBMFFBE-UHFFFAOYSA-N 0.000 description 6
- KIGVOJUDEQXKII-UHFFFAOYSA-N 4-bromo-n-(4-bromophenyl)-n-phenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 KIGVOJUDEQXKII-UHFFFAOYSA-N 0.000 description 6
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 6
- 125000005595 acetylacetonate group Chemical group 0.000 description 6
- 238000002484 cyclic voltammetry Methods 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 229910003437 indium oxide Inorganic materials 0.000 description 6
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 6
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 6
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 229910001930 tungsten oxide Inorganic materials 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- 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 5
- 239000000956 alloy Substances 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 150000001649 bromium compounds Chemical class 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 5
- 230000005284 excitation Effects 0.000 description 5
- 230000005283 ground state Effects 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- 239000012212 insulator Substances 0.000 description 5
- 229910052741 iridium Inorganic materials 0.000 description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 238000005381 potential energy Methods 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- 238000010189 synthetic method Methods 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- 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 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium 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
- 238000005192 partition Methods 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 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
- SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 102100025982 BMP/retinoic acid-inducible neural-specific protein 1 Human genes 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 0 CC(*)c1c(*)c(*)c(*)c(**)c1*#C Chemical compound CC(*)c1c(*)c(*)c(*)c(**)c1*#C 0.000 description 3
- 101000933342 Homo sapiens BMP/retinoic acid-inducible neural-specific protein 1 Proteins 0.000 description 3
- 101000715194 Homo sapiens Cell cycle and apoptosis regulator protein 2 Proteins 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 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
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 230000000295 complement effect Effects 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 229920000736 dendritic polymer Polymers 0.000 description 3
- 238000005137 deposition process Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 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 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 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 3
- 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 3
- BKJULDLPGWGCHY-UHFFFAOYSA-N n,n-bis(4-bromophenyl)-4-phenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(Br)C=C1 BKJULDLPGWGCHY-UHFFFAOYSA-N 0.000 description 3
- AFDFEVPHXYRVDH-UHFFFAOYSA-N n-(4-bromophenyl)-n,4-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 AFDFEVPHXYRVDH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 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 3
- 239000003566 sealing material Substances 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 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 3
- 229910001935 vanadium oxide Inorganic materials 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- 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 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 2
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 2
- OCQFHFNWMCLWKC-UHFFFAOYSA-N 1-n,4-n,4-n-triphenylbenzene-1,4-diamine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 OCQFHFNWMCLWKC-UHFFFAOYSA-N 0.000 description 2
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- 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
- ZULHHMJFLPUTMR-UHFFFAOYSA-N 2-[2,6-bis[2-(6-methoxy-4,4,10,10-tetramethyl-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl)ethenyl]pyran-4-ylidene]propanedinitrile Chemical compound CC1(C)CCN2CCC(C)(C)C3=C2C1=CC(C=CC=1OC(=CC(C=1)=C(C#N)C#N)C=CC=1C(=C2C(C)(C)CCN4C2=C(C(CC4)(C)C)C=1)OC)=C3OC ZULHHMJFLPUTMR-UHFFFAOYSA-N 0.000 description 2
- QUOSAXMWQSSMJW-UHFFFAOYSA-N 2-[2,6-bis[2-[4-(dimethylamino)phenyl]ethenyl]pyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=CC(=C(C#N)C#N)C=C(C=CC=2C=CC(=CC=2)N(C)C)O1 QUOSAXMWQSSMJW-UHFFFAOYSA-N 0.000 description 2
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 2
- FOHQPHVYYMQJOE-UHFFFAOYSA-N 2-[2-propan-2-yl-6-[2-(4,4,10,10-tetramethyl-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-3-yl)ethenyl]pyran-4-ylidene]propanedinitrile Chemical compound C(C)(C)C=1OC(=CC(C=1)=C(C#N)C#N)C=CC1CN2CCC(C3=C2C(C1(C)C)=CC=C3)(C)C FOHQPHVYYMQJOE-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
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 2
- DGTMWPUYBPWJFO-UHFFFAOYSA-N 4-(4-naphthalen-1-ylphenyl)-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 DGTMWPUYBPWJFO-UHFFFAOYSA-N 0.000 description 2
- YLYPIBBGWLKELC-UHFFFAOYSA-N 4-(dicyanomethylene)-2-methyl-6-(4-(dimethylamino)styryl)-4H-pyran Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-UHFFFAOYSA-N 0.000 description 2
- ZNJRONVKWRHYBF-VOTSOKGWSA-N 4-(dicyanomethylene)-2-methyl-6-julolidyl-9-enyl-4h-pyran Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(CCCN2CCC3)=C2C3=C1 ZNJRONVKWRHYBF-VOTSOKGWSA-N 0.000 description 2
- 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 2
- IJVFZXJHZBXCJC-UHFFFAOYSA-N 4-n-[4-(9,10-diphenylanthracen-2-yl)phenyl]-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=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 IJVFZXJHZBXCJC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- UOOBIWAELCOCHK-BQYQJAHWSA-N 870075-87-9 Chemical compound O1C(C(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 UOOBIWAELCOCHK-BQYQJAHWSA-N 0.000 description 2
- 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 2
- 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 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910017073 AlLi Inorganic materials 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-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
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 108091006149 Electron carriers Proteins 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- VUMVABVDHWICAZ-UHFFFAOYSA-N N-phenyl-N-[4-[4-[N-(9,9'-spirobi[fluorene]-2-yl)anilino]phenyl]phenyl]-9,9'-spirobi[fluorene]-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4(C5=CC=CC=C5C5=CC=CC=C54)C4=CC=CC=C4C3=CC=2)C=C1 VUMVABVDHWICAZ-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DIMXHEBVSFQXFW-UHFFFAOYSA-L [Ir+3].C1(=CC=CC=C1)C1(NC=CC=C1)C(=O)[O-].C1(=CC=CC=C1)C1(NC=CC=C1)C(=O)[O-] Chemical compound [Ir+3].C1(=CC=CC=C1)C1(NC=CC=C1)C(=O)[O-].C1(=CC=CC=C1)C1(NC=CC=C1)C(=O)[O-] DIMXHEBVSFQXFW-UHFFFAOYSA-L 0.000 description 2
- YTONQJIHQVWZPO-UHFFFAOYSA-N [Ir+3].C1(=CC=CC=C1)C1=NC=C(N=C1C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C1=NC=C(N=C1C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Ir+3].C1(=CC=CC=C1)C1=NC=C(N=C1C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C1=NC=C(N=C1C1=CC=CC=C1)C1=CC=CC=C1 YTONQJIHQVWZPO-UHFFFAOYSA-N 0.000 description 2
- BERJZCNISREQJL-UHFFFAOYSA-L [Ir+3].FC1=CC=C(C=C1)C1(NC2=CC=CC=C2N=C1C1=CC=C(C=C1)F)C(=O)[O-].FC1=CC=C(C=C1)C1(NC2=CC=CC=C2N=C1C1=CC=C(C=C1)F)C(=O)[O-] Chemical compound [Ir+3].FC1=CC=C(C=C1)C1(NC2=CC=CC=C2N=C1C1=CC=C(C=C1)F)C(=O)[O-].FC1=CC=C(C=C1)C1(NC2=CC=CC=C2N=C1C1=CC=C(C=C1)F)C(=O)[O-] BERJZCNISREQJL-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 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 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- HXWWMGJBPGRWRS-UHFFFAOYSA-N b2738 Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1C=CC1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052804 chromium Inorganic materials 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
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- JRUYYVYCSJCVMP-UHFFFAOYSA-N coumarin 30 Chemical compound C1=CC=C2N(C)C(C=3C4=CC=C(C=C4OC(=O)C=3)N(CC)CC)=NC2=C1 JRUYYVYCSJCVMP-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- AIZHGNQYRBRXOZ-UHFFFAOYSA-K iridium(3+) 2-phenyl-1H-pyridine-2-carboxylate Chemical compound [Ir+3].C1(=CC=CC=C1)C1(NC=CC=C1)C(=O)[O-].C1(=CC=CC=C1)C1(NC=CC=C1)C(=O)[O-].C1(=CC=CC=C1)C1(NC=CC=C1)C(=O)[O-] AIZHGNQYRBRXOZ-UHFFFAOYSA-K 0.000 description 2
- NCCYEOZLSGJEDF-UHFFFAOYSA-N n,n,9-triphenyl-10h-anthracen-9-amine Chemical compound C12=CC=CC=C2CC2=CC=CC=C2C1(C=1C=CC=CC=1)N(C=1C=CC=CC=1)C1=CC=CC=C1 NCCYEOZLSGJEDF-UHFFFAOYSA-N 0.000 description 2
- RVHDEFQSXAYURV-UHFFFAOYSA-N n-[4-(9,10-diphenylanthracen-2-yl)phenyl]-n,9-diphenylcarbazol-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=C3C(C=4C=CC=CC=4)=C4C=CC=CC4=C(C=4C=CC=CC=4)C3=CC=2)C=C1 RVHDEFQSXAYURV-UHFFFAOYSA-N 0.000 description 2
- KUGSVDXBPQUXKX-UHFFFAOYSA-N n-[9,10-bis(2-phenylphenyl)anthracen-2-yl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(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=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 KUGSVDXBPQUXKX-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000001225 nuclear magnetic resonance method Methods 0.000 description 2
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 2
- 230000033116 oxidation-reduction process Effects 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 238000001420 photoelectron spectroscopy Methods 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003980 solgel method Methods 0.000 description 2
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 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
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- RTSZQXSYCGBHMO-UHFFFAOYSA-N 1,2,4-trichloro-3-prop-1-ynoxybenzene Chemical compound CC#COC1=C(Cl)C=CC(Cl)=C1Cl RTSZQXSYCGBHMO-UHFFFAOYSA-N 0.000 description 1
- CGRXLSREVBEJGS-UHFFFAOYSA-N 1,2-dibutyl-9,10-bis(2-naphthalen-1-ylphenyl)anthracene Chemical compound C(CCC)C1=C(C2=C(C3=CC=CC=C3C(=C2C=C1)C1=C(C=CC=C1)C1=CC=CC2=CC=CC=C12)C1=C(C=CC=C1)C1=CC=CC2=CC=CC=C12)CCCC CGRXLSREVBEJGS-UHFFFAOYSA-N 0.000 description 1
- KNRVCICRZJAEAQ-UHFFFAOYSA-N 1-(4-bromophenyl)-4-phenylnaphthalene Chemical compound C1=CC(Br)=CC=C1C(C1=CC=CC=C11)=CC=C1C1=CC=CC=C1 KNRVCICRZJAEAQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XCGVNJBBWRPIPZ-UHFFFAOYSA-N 1-[4-(4-bromophenyl)phenyl]naphthalene Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=2C3=CC=CC=C3C=CC=2)C=C1 XCGVNJBBWRPIPZ-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- UTQUFKAPHZAOQK-UHFFFAOYSA-N 1-n,1-n,2-n,2-n,3-n,3-n,4-n,4-n-octakis-phenylbenzene-1,2,3,4-tetramine Chemical compound C1=CC=CC=C1N(C=1C(=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 UTQUFKAPHZAOQK-UHFFFAOYSA-N 0.000 description 1
- XOYZGLGJSAZOAG-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-[4-[4-(n-[4-(n-phenylanilino)phenyl]anilino)phenyl]phenyl]benzene-1,4-diamine Chemical group C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 XOYZGLGJSAZOAG-UHFFFAOYSA-N 0.000 description 1
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 1
- FQNVFRPAQRVHKO-UHFFFAOYSA-N 1-n,4-n-bis(4-methylphenyl)-1-n,4-n-diphenylbenzene-1,4-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(C)=CC=1)C1=CC=CC=C1 FQNVFRPAQRVHKO-UHFFFAOYSA-N 0.000 description 1
- OOWLPGTVRWFLCX-UHFFFAOYSA-N 2,3,6,7-tetramethyl-9,10-dinaphthalen-1-ylanthracene Chemical compound C1=CC=C2C(C=3C4=CC(C)=C(C)C=C4C(C=4C5=CC=CC=C5C=CC=4)=C4C=C(C(=CC4=3)C)C)=CC=CC2=C1 OOWLPGTVRWFLCX-UHFFFAOYSA-N 0.000 description 1
- JEBPFDQAOYARIB-UHFFFAOYSA-N 2,3,6,7-tetramethyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C=3C4=CC(C)=C(C)C=C4C(C=4C=C5C=CC=CC5=CC=4)=C4C=C(C(=CC4=3)C)C)=CC=C21 JEBPFDQAOYARIB-UHFFFAOYSA-N 0.000 description 1
- XANIFASCQKHXRC-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol zinc Chemical compound [Zn].Oc1ccccc1-c1nc2ccccc2s1.Oc1ccccc1-c1nc2ccccc2s1 XANIFASCQKHXRC-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- IZJOTDOLRQTPHC-UHFFFAOYSA-N 2-(4-carbazol-9-ylphenyl)-5-phenyl-1,3,4-oxadiazole Chemical compound C1=CC=CC=C1C1=NN=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)O1 IZJOTDOLRQTPHC-UHFFFAOYSA-N 0.000 description 1
- CRGSMSNUTNRNQM-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=CO1 CRGSMSNUTNRNQM-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- ONMVVYFKZFORGI-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-1-ylanthracene Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=C(C=4C5=CC=CC=C5C=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=CC2=C1 ONMVVYFKZFORGI-UHFFFAOYSA-N 0.000 description 1
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 1
- WBPXZSIKOVBSAS-UHFFFAOYSA-N 2-tert-butylanthracene Chemical compound C1=CC=CC2=CC3=CC(C(C)(C)C)=CC=C3C=C21 WBPXZSIKOVBSAS-UHFFFAOYSA-N 0.000 description 1
- GRTDQSRHHHDWSQ-UHFFFAOYSA-N 3,6-diphenyl-9-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=2C3=CC(=CC=2)C=2C=CC=CC=2)C3=C1 GRTDQSRHHHDWSQ-UHFFFAOYSA-N 0.000 description 1
- TVMBOHMLKCZFFW-UHFFFAOYSA-N 3-N,6-N,9-triphenyl-3-N,6-N-bis(9-phenylcarbazol-3-yl)carbazole-3,6-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC(=CC=C3N(C=3C=CC=CC=3)C2=CC=1)N(C=1C=CC=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 TVMBOHMLKCZFFW-UHFFFAOYSA-N 0.000 description 1
- 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
- LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical compound NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- QYNTUCBQEHUHCS-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n-[4-[4-(n-[4-(n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-1-n,4-n-diphenylbenzene-1,4-diamine Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 QYNTUCBQEHUHCS-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
- NKEZXXDRXPPROK-UHFFFAOYSA-N 9,10-bis(2-naphthalen-1-ylphenyl)anthracene Chemical compound C12=CC=CC=C2C(C2=CC=CC=C2C=2C3=CC=CC=C3C=CC=2)=C(C=CC=C2)C2=C1C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 NKEZXXDRXPPROK-UHFFFAOYSA-N 0.000 description 1
- YTSGZCWSEMDTBC-UHFFFAOYSA-N 9,10-bis(4-methylnaphthalen-1-yl)anthracene Chemical compound C12=CC=CC=C2C(C)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C)C2=CC=CC=C12 YTSGZCWSEMDTBC-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- RIWPZERARJLOBV-UHFFFAOYSA-N 9-anthracen-9-yl-1-(2,3,4,5,6-pentakis-phenylphenyl)anthracene Chemical group c1ccc(cc1)-c1c(-c2ccccc2)c(-c2ccccc2)c(-c2cccc3cc4ccccc4c(-c4c5ccccc5cc5ccccc45)c23)c(-c2ccccc2)c1-c1ccccc1 RIWPZERARJLOBV-UHFFFAOYSA-N 0.000 description 1
- NFHBACRUEJNXAB-UHFFFAOYSA-N 9-anthracen-9-yl-1-(2-phenylphenyl)anthracene Chemical group C1(=CC=CC=C1)C1=C(C=CC=C1)C1=CC=CC2=CC3=CC=CC=C3C(=C12)C=1C2=CC=CC=C2C=C2C=CC=CC=12 NFHBACRUEJNXAB-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
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- SDVBSUJVQVRMPV-UHFFFAOYSA-N C(C)(CC)C1=CC=CC2=C(C3=CC=CC=C3C(=C12)C1=CC2=CC=CC=C2C=C1)C1=CC2=CC=CC=C2C=C1 Chemical compound C(C)(CC)C1=CC=CC2=C(C3=CC=CC=C3C(=C12)C1=CC2=CC=CC=C2C=C1)C1=CC2=CC=CC=C2C=C1 SDVBSUJVQVRMPV-UHFFFAOYSA-N 0.000 description 1
- SIDRMTWIAZRYKS-UHFFFAOYSA-N C(C)(CC)C1=CC=CC2=C(C3=CC=CC=C3C(=C12)C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1 Chemical compound C(C)(CC)C1=CC=CC2=C(C3=CC=CC=C3C(=C12)C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1 SIDRMTWIAZRYKS-UHFFFAOYSA-N 0.000 description 1
- ZKHISQHQYQCSJE-UHFFFAOYSA-N C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C(C=C(C=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C(C=C(C=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 ZKHISQHQYQCSJE-UHFFFAOYSA-N 0.000 description 1
- OXZQWMBVJFAZEE-UHFFFAOYSA-N C=[Br]c(cc1)ccc1-c(cc1)ccc1Br Chemical compound C=[Br]c(cc1)ccc1-c(cc1)ccc1Br OXZQWMBVJFAZEE-UHFFFAOYSA-N 0.000 description 1
- PXEPSFXJKPNTCZ-UHFFFAOYSA-N C=[Br]c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1Br Chemical compound C=[Br]c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1Br PXEPSFXJKPNTCZ-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- DKNPRRRKHAEUMW-UHFFFAOYSA-N Iodine aqueous Chemical compound [K+].I[I-]I DKNPRRRKHAEUMW-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910017911 MgIn Inorganic materials 0.000 description 1
- PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 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
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 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 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BLLMMMHXIMRJEC-UHFFFAOYSA-N butan-1-amine;perchloric acid Chemical compound CCCC[NH3+].[O-]Cl(=O)(=O)=O BLLMMMHXIMRJEC-UHFFFAOYSA-N 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000015556 catabolic process Effects 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 150000001846 chrysenes Chemical class 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 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 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- GQDKQZAEQBGVBS-UHFFFAOYSA-N dibenzo[g,p]chrysene Chemical class C1=CC=CC2=C3C4=CC=CC=C4C4=CC=CC=C4C3=C(C=CC=C3)C3=C21 GQDKQZAEQBGVBS-UHFFFAOYSA-N 0.000 description 1
- SURBAJYBTYLRMQ-UHFFFAOYSA-N dioxido(propan-2-yloxy)borane Chemical compound CC(C)OB([O-])[O-] SURBAJYBTYLRMQ-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000010893 electron trap Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- WOYDRSOIBHFMGB-UHFFFAOYSA-N n,9-diphenyl-n-(9-phenylcarbazol-3-yl)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(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 WOYDRSOIBHFMGB-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
- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- COVCYOMDZRYBNM-UHFFFAOYSA-N n-naphthalen-1-yl-9-phenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N1C2=CC=C(N(C=3C=C4C5=CC=CC=C5N(C=5C=CC=CC=5)C4=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 COVCYOMDZRYBNM-UHFFFAOYSA-N 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- 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
-
- H01L27/3209—
-
- H01L51/0052—
-
- H01L51/0059—
-
- H01L51/5012—
-
- H01L51/5016—
-
- H01L51/5048—
-
- H01L51/5278—
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/19—Tandem OLEDs
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
-
- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Inorganic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008129991 | 2008-05-16 | ||
| JPJP-P-2008-129991 | 2008-05-16 | ||
| JPJP-P-2008-300827 | 2008-11-26 | ||
| JP2008300827 | 2008-11-26 | ||
| JPJP-P-2009-022314 | 2009-02-03 | ||
| JP2009022314 | 2009-02-03 | ||
| PCT/JP2009/058787 WO2009139358A1 (en) | 2008-05-16 | 2009-04-30 | Triarylamine derivative, light-emitting substance, light-emitting element, light-emitting device, and electronic device |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107028253A Division KR20110022605A (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177014222A Division KR101915453B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20160093116A KR20160093116A (ko) | 2016-08-05 |
| KR101742971B1 true KR101742971B1 (ko) | 2017-06-02 |
Family
ID=41315523
Family Applications (12)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167020847A Active KR101742971B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020177014222A Active KR101915453B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020237014058A Active KR102794567B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020207018427A Active KR102301756B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020187018388A Ceased KR20180077315A (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체 |
| KR1020127016394A Active KR101453383B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020217027723A Active KR102358745B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020227040831A Active KR102528027B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020227002516A Active KR102472283B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020107028253A Ceased KR20110022605A (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020197011300A Active KR102115154B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020207002432A Active KR102129241B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
Family Applications After (11)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177014222A Active KR101915453B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020237014058A Active KR102794567B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020207018427A Active KR102301756B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020187018388A Ceased KR20180077315A (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체 |
| KR1020127016394A Active KR101453383B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020217027723A Active KR102358745B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020227040831A Active KR102528027B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020227002516A Active KR102472283B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020107028253A Ceased KR20110022605A (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020197011300A Active KR102115154B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| KR1020207002432A Active KR102129241B1 (ko) | 2008-05-16 | 2009-04-30 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
Country Status (6)
| Country | Link |
|---|---|
| US (7) | US8182933B2 (enExample) |
| JP (9) | JP5420310B2 (enExample) |
| KR (12) | KR101742971B1 (enExample) |
| CN (2) | CN102942492B (enExample) |
| TW (1) | TWI469954B (enExample) |
| WO (1) | WO2009139358A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2757094A1 (en) | 2007-12-03 | 2014-07-23 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole derivative, and light-emitting element, light-emitting device, and electronic device uing carbazole derivative |
| KR101742971B1 (ko) | 2008-05-16 | 2017-06-02 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| TWI583253B (zh) | 2009-01-21 | 2017-05-11 | 半導體能源研究所股份有限公司 | 發光元件,發光裝置以及電子裝置 |
| KR20180126629A (ko) * | 2011-12-12 | 2018-11-27 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
| EP3460864B1 (de) * | 2012-03-15 | 2025-06-04 | Merck Patent GmbH | Elektronische vorrichtungen |
| DE102012102910B4 (de) * | 2012-04-03 | 2016-09-22 | Novaled Ag | Vertikaler organischer Transistor und Verfahren zum Herstellen |
| KR101990553B1 (ko) | 2012-04-17 | 2019-06-19 | 삼성디스플레이 주식회사 | 신규한 유기 발광 소자용 화합물 및 이를 포함한 유기 발광 소자 |
| US9553278B2 (en) * | 2012-06-01 | 2017-01-24 | Panasonic Intellectual Property Management Co., Ltd. | Organic electroluminsescence element and lighting device |
| KR102079249B1 (ko) * | 2012-06-12 | 2020-02-20 | 삼성디스플레이 주식회사 | 신규한 유기 발광 소자용 화합물 및 이를 포함한 유기 발광 소자 |
| US9209401B2 (en) * | 2012-06-20 | 2015-12-08 | Joled Inc | Method for manufacturing organic EL element, organic EL element, organic EL display panel, organic EL display apparatus, and organic EL light-emitting apparatus |
| KR20150038093A (ko) | 2012-08-03 | 2015-04-08 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 전자 장치 및 조명 장치 |
| KR102197749B1 (ko) | 2013-01-03 | 2021-01-04 | 메르크 파텐트 게엠베하 | 전자 소자용 재료 |
| TWI473780B (zh) | 2014-04-09 | 2015-02-21 | Nat Univ Chung Hsing | 光敏染料化合物以及染料敏化太陽能電池 |
| CN106688119B (zh) * | 2014-07-09 | 2019-07-23 | 保土谷化学工业株式会社 | 有机电致发光器件 |
| US10164194B2 (en) * | 2015-01-26 | 2018-12-25 | Luminescence Technology Corporation | Compound for organic electroluminescent device |
| CN110117267A (zh) | 2016-01-29 | 2019-08-13 | 株式会社半导体能源研究所 | 发光元件、发光装置、电子设备及照明装置 |
| KR102636244B1 (ko) * | 2016-03-30 | 2024-02-15 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 |
| TWI804474B (zh) | 2016-09-14 | 2023-06-11 | 日商半導體能源研究所股份有限公司 | 有機化合物、發光元件、發光裝置、電子裝置及照明設備 |
| KR102701648B1 (ko) | 2016-12-28 | 2024-09-03 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 소자, 발광 장치, 전자 기기, 표시 장치, 및 조명 장치 |
| JP6339749B1 (ja) | 2017-04-07 | 2018-06-06 | 株式会社半導体エネルギー研究所 | 有機化合物、発光素子、発光装置、電子機器、照明装置、及び電子デバイス |
| DE112018000021B4 (de) | 2017-04-07 | 2022-07-07 | Semiconductor Energy Laboratory Co., Ltd. | Organische Verbindung und deren Verwendung in Licht emittierenden Elementen, Licht emittierenden Vorrichtungen, elektronischen Vorrichtungen, Anzeigevorrichtungen und Beleuchtungsvorrichtungen |
| US10879471B2 (en) | 2017-05-10 | 2020-12-29 | Samsung Display Co., Ltd. | Organic electroluminescence device and amine compound for organic electroluminescence device |
| JP2019003928A (ja) * | 2017-06-16 | 2019-01-10 | パナソニックIpマネジメント株式会社 | フロー電池 |
| KR102801558B1 (ko) * | 2018-06-11 | 2025-05-08 | 엘지디스플레이 주식회사 | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
| CN108658800A (zh) * | 2018-06-21 | 2018-10-16 | 中国林业科学研究院林产化学工业研究所 | 一类基于脱氢枞酸芳环二取代的化合物及其制备方法 |
| CN108658801A (zh) * | 2018-06-21 | 2018-10-16 | 中国林业科学研究院林产化学工业研究所 | 一类基于脱氢枞酸芳环的化合物及其制备方法 |
| JP7450539B2 (ja) | 2018-07-31 | 2024-03-15 | 株式会社半導体エネルギー研究所 | 有機化合物および発光素子 |
| CN111448679B (zh) * | 2018-08-17 | 2023-11-17 | 株式会社Lg化学 | 有机发光器件 |
| JP2020136517A (ja) * | 2019-02-20 | 2020-08-31 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
| WO2020189316A1 (ja) * | 2019-03-15 | 2020-09-24 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 |
| EP4043431A4 (en) | 2019-10-11 | 2023-11-01 | Idemitsu Kosan Co., Ltd | COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENTS, ORGANIC ELECTROLUMINESCENT ELEMENT THEREFROM AND ELECTRONIC DEVICE |
| EP4043430A4 (en) | 2019-10-11 | 2023-12-20 | Idemitsu Kosan Co., Ltd. | COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENTS, ORGANIC ELECTROLUMINESCENT ELEMENT AND ELECTRONIC DEVICE |
| TW202222772A (zh) * | 2020-10-16 | 2022-06-16 | 日商保土谷化學工業股份有限公司 | 芳香胺化合物、有機電致發光元件及電子機器 |
| KR20220122860A (ko) | 2021-02-26 | 2022-09-05 | 삼성디스플레이 주식회사 | 발광 소자 및 이를 포함한 전자 장치 |
| CN117343078A (zh) | 2021-11-25 | 2024-01-05 | 北京夏禾科技有限公司 | 有机电致发光材料和器件 |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
| JP2951434B2 (ja) | 1991-04-18 | 1999-09-20 | 三菱製紙株式会社 | 電子写真感光体 |
| US5415962A (en) | 1992-04-23 | 1995-05-16 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, electrophotographic apparatus using same and device unit using same |
| JP3278252B2 (ja) * | 1993-08-12 | 2002-04-30 | 靖彦 城田 | 有機el素子 |
| JP4140986B2 (ja) | 1997-02-14 | 2008-08-27 | 出光興産株式会社 | 有機電界発光素子 |
| JP3689546B2 (ja) * | 1997-12-25 | 2005-08-31 | キヤノン株式会社 | 電子写真感光体、プロセスカートリッジ及び電子写真装置 |
| US6656608B1 (en) | 1998-12-25 | 2003-12-02 | Konica Corporation | Electroluminescent material, electroluminescent element and color conversion filter |
| JP3968933B2 (ja) | 1998-12-25 | 2007-08-29 | コニカミノルタホールディングス株式会社 | エレクトロルミネッセンス素子 |
| US7871713B2 (en) | 1998-12-25 | 2011-01-18 | Konica Corporation | Electroluminescent material, electroluminescent element and color conversion filter |
| KR20050084516A (ko) * | 1998-12-28 | 2005-08-26 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자 |
| JP3855587B2 (ja) * | 2000-03-27 | 2006-12-13 | コニカミノルタホールディングス株式会社 | 熱記録媒体、追記型情報記録要素、記録方法、情報の読み出し方法、有機エレクトロルミネッセンス素子の多色化方法、温度測定方法及び不可逆性温度マーカー |
| JP4788078B2 (ja) * | 2000-09-20 | 2011-10-05 | 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、有機エレクトロルミネッセンス素子材料および表示装置 |
| EP1191821B1 (en) | 2000-09-25 | 2009-05-27 | Konica Corporation | Organic electroluminescent element and organic electroluminescent material used therefor |
| JP4951829B2 (ja) * | 2000-09-25 | 2012-06-13 | 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および表示装置 |
| JP4770033B2 (ja) | 2001-02-13 | 2011-09-07 | 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 |
| JP4686895B2 (ja) * | 2001-04-27 | 2011-05-25 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
| JP2003055320A (ja) * | 2001-08-16 | 2003-02-26 | Idemitsu Kosan Co Ltd | 芳香族ジアミン誘導体の製造方法 |
| EP1289015B1 (en) | 2001-08-28 | 2012-05-23 | Konica Corporation | Multicolor light emission apparatus and manufacturing method thereof |
| JP4477803B2 (ja) | 2001-09-19 | 2010-06-09 | 三井化学株式会社 | アミン化合物および該化合物を含有する有機電界発光素子 |
| JP5135660B2 (ja) | 2001-09-27 | 2013-02-06 | 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 |
| JP2004047443A (ja) * | 2002-05-15 | 2004-02-12 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及びカラー表示装置 |
| TWI282701B (en) | 2002-08-16 | 2007-06-11 | Au Optronics Corp | Organic electroluminescent device |
| US7232617B2 (en) * | 2003-02-04 | 2007-06-19 | Cityu Research Limited | Electroluminescent devices |
| US7271406B2 (en) * | 2003-04-15 | 2007-09-18 | 3M Innovative Properties Company | Electron transport agents for organic electronic devices |
| 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 |
| DE112005002603A5 (de) | 2004-08-13 | 2007-08-09 | Novaled Gmbh | Schichtanordnung für ein Lichtemittierendes Bauelement |
| US20060091359A1 (en) | 2004-10-29 | 2006-05-04 | Jun-Liang Lai | Organic light emitting compounds for a blue-light electroluminescent device |
| US8629613B2 (en) | 2005-01-05 | 2014-01-14 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent device using same |
| EP2371810A1 (en) | 2005-01-05 | 2011-10-05 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent device using same |
| JP2006310351A (ja) | 2005-04-26 | 2006-11-09 | Sony Corp | 有機電界発光素子および表示装置 |
| DE102005023437A1 (de) | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
| JP2007015933A (ja) | 2005-07-05 | 2007-01-25 | Sony Corp | アントラセン誘導体の合成方法、有機電界発光素子、および表示装置 |
| WO2007058127A1 (ja) * | 2005-11-16 | 2007-05-24 | Idemitsu Kosan Co., Ltd. | 芳香族アミ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 |
| US20070145888A1 (en) | 2005-11-16 | 2007-06-28 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivatives and organic electroluminescence device using the same |
| CN101296895A (zh) | 2005-11-16 | 2008-10-29 | 出光兴产株式会社 | 芳香族胺衍生物以及应用该衍生物的有机电致发光元件 |
| EP1808909A1 (de) | 2006-01-11 | 2007-07-18 | Novaled AG | Elekrolumineszente Lichtemissionseinrichtung |
| US9112170B2 (en) | 2006-03-21 | 2015-08-18 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, and electronic device |
| JP5242016B2 (ja) | 2006-03-31 | 2013-07-24 | 双葉電子工業株式会社 | 有機el素子用化合物及び有機el素子 |
| WO2007125714A1 (ja) | 2006-04-26 | 2007-11-08 | Idemitsu Kosan Co., Ltd. | 芳香族アミ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 |
| US8623522B2 (en) | 2006-04-26 | 2014-01-07 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and electroluminescence device using the same |
| WO2008035517A1 (fr) | 2006-09-22 | 2008-03-27 | Idemitsu Kosan Co., Ltd. | Dérivés d'amine aromatique et dispositif organique électroluminescent fabriqué en les utilisant |
| JP2008120769A (ja) * | 2006-11-15 | 2008-05-29 | Bando Chem Ind Ltd | 新規な芳香族第3級アミン類とその利用 |
| KR101030021B1 (ko) | 2007-04-13 | 2011-04-20 | 제일모직주식회사 | 분자 내에 정공 수송기와 전자 수송기를 동시에 가지는바이폴라 특성의 유기화합물을 포함하는 유기광전소자용재료 및 이를 이용한 유기광전소자 |
| JP5125213B2 (ja) * | 2007-05-08 | 2013-01-23 | 東ソー株式会社 | 新規なトリアリールアミンポリマー、その製造方法及び用途 |
| EP2757094A1 (en) * | 2007-12-03 | 2014-07-23 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole derivative, and light-emitting element, light-emitting device, and electronic device uing carbazole derivative |
| KR101742971B1 (ko) | 2008-05-16 | 2017-06-02 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 트리아릴아민 유도체, 발광 물질, 발광 소자, 발광 장치 및 전자 기기 |
| JP2010186983A (ja) * | 2009-01-19 | 2010-08-26 | Sony Corp | 有機電界発光素子および表示装置 |
| JP6179265B2 (ja) | 2013-08-12 | 2017-08-16 | 東洋インキScホールディングス株式会社 | 接着剤組成物、電池用包装材、及び電池用容器 |
-
2009
- 2009-04-30 KR KR1020167020847A patent/KR101742971B1/ko active Active
- 2009-04-30 WO PCT/JP2009/058787 patent/WO2009139358A1/en not_active Ceased
- 2009-04-30 KR KR1020177014222A patent/KR101915453B1/ko active Active
- 2009-04-30 KR KR1020237014058A patent/KR102794567B1/ko active Active
- 2009-04-30 KR KR1020207018427A patent/KR102301756B1/ko active Active
- 2009-04-30 KR KR1020187018388A patent/KR20180077315A/ko not_active Ceased
- 2009-04-30 KR KR1020127016394A patent/KR101453383B1/ko active Active
- 2009-04-30 KR KR1020217027723A patent/KR102358745B1/ko active Active
- 2009-04-30 KR KR1020227040831A patent/KR102528027B1/ko active Active
- 2009-04-30 CN CN201210279619.1A patent/CN102942492B/zh active Active
- 2009-04-30 KR KR1020227002516A patent/KR102472283B1/ko active Active
- 2009-04-30 CN CN200980118355.8A patent/CN102026957B/zh active Active
- 2009-04-30 KR KR1020107028253A patent/KR20110022605A/ko not_active Ceased
- 2009-04-30 KR KR1020197011300A patent/KR102115154B1/ko active Active
- 2009-04-30 KR KR1020207002432A patent/KR102129241B1/ko active Active
- 2009-05-12 US US12/464,506 patent/US8182933B2/en active Active
- 2009-05-14 JP JP2009117378A patent/JP5420310B2/ja active Active
- 2009-05-15 TW TW98116217A patent/TWI469954B/zh active
-
2012
- 2012-05-17 US US13/474,104 patent/US8940416B2/en active Active
-
2013
- 2013-11-20 JP JP2013239529A patent/JP2014139156A/ja not_active Withdrawn
-
2015
- 2015-01-26 US US14/605,286 patent/US9540315B2/en active Active
- 2015-08-26 JP JP2015166358A patent/JP2016041691A/ja not_active Withdrawn
-
2016
- 2016-10-28 JP JP2016211215A patent/JP2017052767A/ja not_active Withdrawn
-
2017
- 2017-01-05 US US15/399,408 patent/US10804471B2/en active Active
- 2017-09-29 JP JP2017189800A patent/JP2018030867A/ja not_active Withdrawn
-
2019
- 2019-02-28 JP JP2019035677A patent/JP6858210B2/ja active Active
-
2020
- 2020-10-08 US US17/065,762 patent/US11678568B2/en active Active
-
2021
- 2021-01-19 JP JP2021006459A patent/JP7187589B2/ja active Active
-
2022
- 2022-11-30 JP JP2022191573A patent/JP7524281B2/ja active Active
-
2023
- 2023-05-22 US US18/200,370 patent/US11980087B2/en active Active
-
2024
- 2024-05-02 US US18/653,569 patent/US12490650B2/en active Active
- 2024-07-17 JP JP2024113987A patent/JP7781975B2/ja active Active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7781975B2 (ja) | 発光素子 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A107 | Divisional application of patent | ||
| A201 | Request for examination | ||
| PA0104 | Divisional application for international application |
Comment text: Divisional Application for International Patent Patent event code: PA01041R01D Patent event date: 20160729 Application number text: 1020107028253 Filing date: 20101215 |
|
| PA0201 | Request for examination | ||
| PG1501 | Laying open of application | ||
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20160929 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20170227 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20170529 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20170530 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| PR1001 | Payment of annual fee |
Payment date: 20210428 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20230418 Start annual number: 7 End annual number: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20250403 Start annual number: 9 End annual number: 9 |