JP2008525608A - 硬質アミン - Google Patents
硬質アミン Download PDFInfo
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- JP2008525608A JP2008525608A JP2007548891A JP2007548891A JP2008525608A JP 2008525608 A JP2008525608 A JP 2008525608A JP 2007548891 A JP2007548891 A JP 2007548891A JP 2007548891 A JP2007548891 A JP 2007548891A JP 2008525608 A JP2008525608 A JP 2008525608A
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- Prior art keywords
- monomer
- optionally substituted
- conjugated polymer
- independently selected
- polymer
- 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.)
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- 150000001412 amines Chemical class 0.000 title description 4
- 239000000178 monomer Substances 0.000 claims abstract description 87
- 229920000547 conjugated polymer Polymers 0.000 claims abstract description 44
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 27
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims description 110
- 229920000642 polymer Polymers 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000004429 atom Chemical group 0.000 claims description 33
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 230000005525 hole transport Effects 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 150000004696 coordination complex Chemical class 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 230000005693 optoelectronics Effects 0.000 claims description 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 11
- 125000004001 thioalkyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 229910052796 boron Inorganic materials 0.000 claims description 7
- -1 boron ester Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000003780 insertion Methods 0.000 claims description 6
- 230000037431 insertion Effects 0.000 claims description 6
- 239000004065 semiconductor Substances 0.000 claims description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 3
- 150000001638 boron Chemical class 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 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 claims description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 48
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000004770 highest occupied molecular orbital Methods 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 230000006870 function Effects 0.000 description 10
- 0 *C([C@]1N=CC=CC1)=CC=CC=C Chemical compound *C([C@]1N=CC=CC1)=CC=CC=C 0.000 description 9
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 description 9
- 239000003446 ligand Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000011970 polystyrene sulfonate Substances 0.000 description 7
- 229960002796 polystyrene sulfonate Drugs 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 125000005259 triarylamine group Chemical group 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000005264 aryl amine group Chemical group 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 239000008393 encapsulating agent Substances 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical group [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229920002098 polyfluorene Polymers 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical class [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- 238000004608 ZINDO calculation Methods 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Chemical compound O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910052740 iodine Chemical class 0.000 description 2
- 239000011630 iodine Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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
- OIBMLOZWRCLWCQ-UHFFFAOYSA-N (2-tert-butylphenyl)-diphenylphosphane Chemical compound CC(C)(C)C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 OIBMLOZWRCLWCQ-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- PZWLRLIAVLSBQU-UHFFFAOYSA-N 1,2-dioctyl-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(CCCCCCCC)C(CCCCCCCC)=C3CC2=C1 PZWLRLIAVLSBQU-UHFFFAOYSA-N 0.000 description 1
- WNLMYIPOMNQVLC-UHFFFAOYSA-N 1,4-dioctylbenzene Chemical compound CCCCCCCCC1=CC=C(CCCCCCCC)C=C1 WNLMYIPOMNQVLC-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- BKPDQETYXNGMRE-UHFFFAOYSA-N 1-tert-butyl-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(C(C)(C)C)=CC=C2 BKPDQETYXNGMRE-UHFFFAOYSA-N 0.000 description 1
- BSEYNMIKUJJMGH-UHFFFAOYSA-N 3-hydroxybenzo[h]quinoline-2-carboxylic acid Chemical compound C1=CC=C2C(N=C(C(=C3)O)C(=O)O)=C3C=CC2=C1 BSEYNMIKUJJMGH-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- BGBUEPYWYDNJQN-UHFFFAOYSA-N Cc(cc1)ccc1Nc(cc1)ccc1Br Chemical compound Cc(cc1)ccc1Nc(cc1)ccc1Br BGBUEPYWYDNJQN-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Natural products CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- OLBVUFHMDRJKTK-UHFFFAOYSA-N [N].[O] Chemical compound [N].[O] OLBVUFHMDRJKTK-UHFFFAOYSA-N 0.000 description 1
- QRSFFHRCBYCWBS-UHFFFAOYSA-N [O].[O] Chemical compound [O].[O] QRSFFHRCBYCWBS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- XMVAAAZAGOWVON-UHFFFAOYSA-N aluminum barium Chemical compound [Al].[Ba] XMVAAAZAGOWVON-UHFFFAOYSA-N 0.000 description 1
- UCOHKZKRNWNULS-UHFFFAOYSA-N aminocyanamide Chemical compound NNC#N UCOHKZKRNWNULS-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- ZGDJMMPBPMJJBR-UHFFFAOYSA-N bis(1H-indol-2-yl)diazene Chemical compound c1c(N=Nc2cc3ccccc3[nH]2)[nH]c2ccccc12 ZGDJMMPBPMJJBR-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000005620 boronic acid group Chemical class 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N c(cc1)ccc1-c1nccc2ccccc12 Chemical compound c(cc1)ccc1-c1nccc2ccccc12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N c(cc1)ccc1-c1ncccc1 Chemical compound c(cc1)ccc1-c1ncccc1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- KSTXZRLNDZADSO-UHFFFAOYSA-N c(cc1)ccc1-c1sc(cccc2)c2[nH]1 Chemical compound c(cc1)ccc1-c1sc(cccc2)c2[nH]1 KSTXZRLNDZADSO-UHFFFAOYSA-N 0.000 description 1
- NRSBAUDUBWMTGL-UHFFFAOYSA-N c1c(-c2ccccn2)[s]c2c1cccc2 Chemical compound c1c(-c2ccccn2)[s]c2c1cccc2 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 description 1
- QLPKTAFPRRIFQX-UHFFFAOYSA-N c1c[s]c(-c2ncccc2)c1 Chemical compound c1c[s]c(-c2ncccc2)c1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N c1ccc2c3ncccc3ccc2c1 Chemical compound c1ccc2c3ncccc3ccc2c1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N c1cnc2c3ncccc3ccc2c1 Chemical compound c1cnc2c3ncccc3ccc2c1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- ICMGJLRWDJYLGU-UHFFFAOYSA-N carbamic acid;2-hydroxybenzoic acid Chemical compound NC(O)=O.OC(=O)C1=CC=CC=C1O ICMGJLRWDJYLGU-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical group [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000004777 chromones Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical group [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
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- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
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- 230000009467 reduction Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical group [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- XTVMZZBLCLWBPM-UHFFFAOYSA-N tert-butylcyclohexane Chemical compound CC(C)(C)C1CCCCC1 XTVMZZBLCLWBPM-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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| GB0502254A GB0502254D0 (en) | 2005-02-03 | 2005-02-03 | Rigid amines |
| PCT/GB2005/005058 WO2006070185A1 (en) | 2004-12-29 | 2005-12-23 | Rigid amines |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008531822A (ja) * | 2005-03-04 | 2008-08-14 | 住友化学株式会社 | ジカルバゾール芳香族アミンポリマー及び電子デバイス |
| JP2008211135A (ja) * | 2007-02-28 | 2008-09-11 | Sumitomo Chemical Co Ltd | 有機発光素子およびその製造方法 |
| JP4874792B2 (ja) * | 2003-06-26 | 2012-02-15 | メルク パテント ゲーエムベーハー | 電界発光用新規材料 |
| JP2012507507A (ja) * | 2008-10-31 | 2012-03-29 | グレイセル・ディスプレイ・インコーポレーテッド | 新規な有機電子材料用化合物及びこれを含む有機電子素子 |
| JP2014068027A (ja) * | 2007-11-08 | 2014-04-17 | Konica Minolta Inc | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| JP2019001878A (ja) * | 2017-06-14 | 2019-01-10 | 住友化学株式会社 | 組成物及びそれを用いた発光素子 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2433509A (en) * | 2005-12-22 | 2007-06-27 | Cambridge Display Tech Ltd | Arylamine polymer |
| DE102006035750A1 (de) * | 2006-07-28 | 2008-01-31 | Polylc Gmbh & Co. Kg | Material zur Herstellung einer Funktionsschicht eines organischen elektronischen Bauelements |
| DE102007023876A1 (de) * | 2007-03-02 | 2008-09-04 | Osram Opto Semiconductors Gmbh | Elektrisches organisches Bauelement und Verfahren zu seiner Herstellung |
| GB2454890B (en) | 2007-11-21 | 2010-08-25 | Limited Cambridge Display Technology | Light-emitting device and materials therefor |
| GB2462314B (en) * | 2008-08-01 | 2011-03-16 | Cambridge Display Tech Ltd | Organic light-emiting materials and devices |
| KR101736973B1 (ko) | 2010-01-15 | 2017-05-17 | 삼성전자주식회사 | 고분자 및 상기 고분자를 포함한 유기 발광 소자 |
| CN103053043B (zh) * | 2010-07-30 | 2016-03-16 | 默克专利有限公司 | 有机电致发光器件 |
| US9397294B2 (en) * | 2011-07-05 | 2016-07-19 | Solvay Usa, Inc. | Vertically phase-separating semiconducting organic material layers |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4874792B2 (ja) * | 2003-06-26 | 2012-02-15 | メルク パテント ゲーエムベーハー | 電界発光用新規材料 |
| JP2008531822A (ja) * | 2005-03-04 | 2008-08-14 | 住友化学株式会社 | ジカルバゾール芳香族アミンポリマー及び電子デバイス |
| JP2008211135A (ja) * | 2007-02-28 | 2008-09-11 | Sumitomo Chemical Co Ltd | 有機発光素子およびその製造方法 |
| JP2014068027A (ja) * | 2007-11-08 | 2014-04-17 | Konica Minolta Inc | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| JP2012507507A (ja) * | 2008-10-31 | 2012-03-29 | グレイセル・ディスプレイ・インコーポレーテッド | 新規な有機電子材料用化合物及びこれを含む有機電子素子 |
| JP2019001878A (ja) * | 2017-06-14 | 2019-01-10 | 住友化学株式会社 | 組成物及びそれを用いた発光素子 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2460358B (en) | 2010-01-13 |
| GB2460358A (en) | 2009-12-02 |
| GB2436996A (en) | 2007-10-10 |
| US20090206731A1 (en) | 2009-08-20 |
| US8415029B2 (en) | 2013-04-09 |
| DE112005003284T5 (de) | 2008-02-14 |
| JP2013209655A (ja) | 2013-10-10 |
| GB2436996B (en) | 2009-12-16 |
| JP5704729B2 (ja) | 2015-04-22 |
| GB0915624D0 (en) | 2009-10-07 |
| WO2006070185A1 (en) | 2006-07-06 |
| US9159929B2 (en) | 2015-10-13 |
| US20130220422A1 (en) | 2013-08-29 |
| DE112005003284B4 (de) | 2016-03-03 |
| GB0712499D0 (en) | 2007-08-08 |
| GB2436996A8 (en) | 2013-12-11 |
| GB2436996B8 (en) | 2013-12-11 |
| DE112005003872A5 (de) | 2016-03-03 |
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