TWI507377B - 茀二聚體和三聚體 - Google Patents
茀二聚體和三聚體 Download PDFInfo
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- TWI507377B TWI507377B TW099119505A TW99119505A TWI507377B TW I507377 B TWI507377 B TW I507377B TW 099119505 A TW099119505 A TW 099119505A TW 99119505 A TW99119505 A TW 99119505A TW I507377 B TWI507377 B TW I507377B
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- aromatic
- cathode
- alkyl
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- 239000013638 trimer Substances 0.000 title description 5
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 230000005693 optoelectronics Effects 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 76
- -1 aryl borate Chemical compound 0.000 description 70
- 125000003118 aryl group Chemical group 0.000 description 42
- 239000000463 material Substances 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 229910052717 sulfur Inorganic materials 0.000 description 14
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 239000001301 oxygen Chemical group 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 11
- 125000000524 functional group Chemical group 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 239000011593 sulfur Chemical group 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 230000004888 barrier function Effects 0.000 description 7
- 125000001188 haloalkyl group Chemical group 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
- 238000004020 luminiscence type Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920002098 polyfluorene Polymers 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000002800 charge carrier Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000002015 acyclic group Chemical group 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 230000031700 light absorption Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000002923 oximes Chemical group 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 4
- 230000006798 recombination Effects 0.000 description 4
- 238000005215 recombination Methods 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 150000007970 thio esters Chemical class 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920000291 Poly(9,9-dioctylfluorene) Polymers 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000001046 green dye Substances 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000001044 red dye Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 229910052714 tellurium Inorganic materials 0.000 description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 2
- 150000003536 tetrazoles Chemical class 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 1
- WSNLVLNJKOLJKZ-UHFFFAOYSA-N 2,7-dibromo-9,9-bis(4-hexoxyphenyl)fluorene Chemical compound C1=CC(OCCCCCC)=CC=C1C1(C=2C=CC(OCCCCCC)=CC=2)C2=CC(Br)=CC=C2C2=CC=C(Br)C=C21 WSNLVLNJKOLJKZ-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- PGDARWFJWJKPLY-UHFFFAOYSA-N 4-[2-[3-[4-(diethylamino)phenyl]-2-phenyl-1,3-dihydropyrazol-5-yl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)N(CC)CC)N(C=2C=CC=CC=2)N1 PGDARWFJWJKPLY-UHFFFAOYSA-N 0.000 description 1
- MVIXNQZIMMIGEL-UHFFFAOYSA-N 4-methyl-n-[4-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MVIXNQZIMMIGEL-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 125000006618 5- to 10-membered aromatic heterocyclic group Chemical group 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 229910018170 Al—Au Inorganic materials 0.000 description 1
- XTOMFMNDPPZOCN-UHFFFAOYSA-N C1(=CC=CC=C1)NNC1=CC=CC=C1.C(C)N(C1=CC=C(C=O)C=C1)CC Chemical compound C1(=CC=CC=C1)NNC1=CC=CC=C1.C(C)N(C1=CC=C(C=O)C=C1)CC XTOMFMNDPPZOCN-UHFFFAOYSA-N 0.000 description 1
- HLWYYNFBQUXPLQ-UHFFFAOYSA-N C1CCC(C#N)(C#N)CC1OC(C)(C)OC1CCCCC1 Chemical compound C1CCC(C#N)(C#N)CC1OC(C)(C)OC1CCCCC1 HLWYYNFBQUXPLQ-UHFFFAOYSA-N 0.000 description 1
- KXSMWPZRKJIOMQ-UHFFFAOYSA-N C=1C=CNC=1.N1N=CC=CC2=CC=CC=C12 Chemical compound C=1C=CNC=1.N1N=CC=CC2=CC=CC=C12 KXSMWPZRKJIOMQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
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- XKTABYOWTSPKHT-UHFFFAOYSA-N N1=CC=CC2=CC=CC=C21.N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound N1=CC=CC2=CC=CC=C21.N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 XKTABYOWTSPKHT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- HDBMWBJHOWINSB-UHFFFAOYSA-N O1C=NCC1.N1C=CC=C1 Chemical compound O1C=NCC1.N1C=CC=C1 HDBMWBJHOWINSB-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- QWLMUBQOQYEELO-UHFFFAOYSA-N [Ru+3].C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 Chemical compound [Ru+3].C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 QWLMUBQOQYEELO-UHFFFAOYSA-N 0.000 description 1
- BWZNMFIGGHVLSV-UHFFFAOYSA-N [Ru].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 Chemical compound [Ru].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 BWZNMFIGGHVLSV-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- GZYYOTJXMDCAJN-UHFFFAOYSA-N cyclohexyloxymethoxycyclohexane Chemical compound C1CCCCC1OCOC1CCCCC1 GZYYOTJXMDCAJN-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- HRHKULZDDYWVBE-UHFFFAOYSA-N indium;oxozinc;tin Chemical compound [In].[Sn].[Zn]=O HRHKULZDDYWVBE-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000011326 mechanical measurement Methods 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 125000004373 methylthiopropyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000003380 quartz crystal microbalance Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 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 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
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- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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- 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
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- 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
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- 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
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- 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
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- 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
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- 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
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
Description
本發明係有關茀二聚體和三聚體。
在OLED裝置中，分別從陰極與陽極注射之電子與電洞在發光層中組合產生單態與三重態激子，其可輻射衰變產生光或非輻射衰變產生熱。就大部分有機分子而言，來自三重態之發光係為一種自旋禁制(spin-forbidden)程序，無法與非輻射衰變模式媲美，因此三重態激子發光性不強。過渡金屬錯合物憑藉著自旋軌道偶合而可以與非輻射途徑媲美之效率輻射衰變。當該等錯合物結合至OLED裝置時，由於該裝置中所產生之單態與三重態激子二者均可發光，故可能達到幾近100%之內部量子效率。
就可溶液加工之OLED裝置而言，過渡金屬錯合物通常藉由摻合或經由共價附接於聚合物主體而與該等聚合主體結合。該等類型裝置之適用聚合主體所具有的三重態能量高於發光性客體過渡金屬錯合物以確保適合能量轉移。當能量轉移激發客體且產生發光現象時，於主體聚合物中產生之三重態激子遷移直到其碰撞發光性客體為止。來自該主體之三重態激子亦可朝陽極或陰極遷移且於該處以非輻射方式猝滅。因此，需要限制三重態激子以使與發光性客體碰撞的機率最大化以及防止朝向電極(特別是陰極)遷移。防止激子朝向陰極遷移的方式之一係在陰極與發光
層之間插入三重態能量大於主體發光層的阻擋層。該阻擋層亦可促使電子從陰極注射且具有良好電子移動性。
簡而言之，在一實施樣態中，本發明有關包括式I之三重態阻擋化合物的光電裝置，特別是OLED，
其中R1於各次出現時獨立為C1-20烴基，且R1之至少一者為R3，R2於各次出現時獨立為C1-20烴基、C1-20烴氧基、C1-20硫醚、C1-20烴基羰氧基或氰基；R3為-R4XR5；R4為直接鍵、C1-20芳基、C1-20芳基烷基、C1-20烷基芳基、C1-20經取代芳基、C1-20經取代芳基烷基、或C1-20經取代烷基芳基；R5為C1-20烴基或碳原子之間含有至少一個S、N、O或P原子的C1-20烴基；R6為C1-20烷基或C1-20經取代烷基；X為-O-、-S-、-COO-、-OOC-、-CSS-、-SSC-、NR6
或PR6；a於各次出現時獨立為0、1或2；且n為0或1。
在另一實施樣態中，本發明有關式Ia之化合物
其中R1於各次出現時獨立為C1-20烴基，且R1之至少一者為R3a，R2於各次出現時獨立為C1-20烴基、C1-20烴氧基、C1-20硫醚、C1-20烴基羰氧基或氰基；R3a為碳原子之間含有至少一個S、N、O或P原子的C1-20烴基；a於各次出現時獨立為0、1或2；且n為0或1。
本發明有關包括以下一系列層之光電裝置：陽極，通常為氧化銦錫(ITO)；電洞注射層，以促使正電荷載子從ITO注射至有機層內；一或多層發光層，電子與電洞於其中重組合而發光；包括式I或Ia之化合物的電子傳輸與三重態阻擋層；以及電子注射陰極。
表1顯示當寡聚物中之茀單元總數改變時之能階排序。由寡聚單元所構成之聚合物亦具有相當的LUMO能級(因此促使電子注射至發光層內)及略深之HOMO能級，因此抑制電洞從發光層遷移。最後，該等材料具有使得能溶液加工製造多層裝置的溶解性質。
因此，式I之化合物極適於用作發光層之三重態能級等於或低於聚茀(T1=2.11eV)的裝置中之三重態阻擋層。
為了符合該等材料促使電子注射及移動性之要求，本發明之光電裝置包括在茀片段的第9位置帶有極性取代基之化合物。因此，在一實施樣態中，本發明有關可用作光電裝置中之三重態阻擋材料的式I之化合物。該等極性取代基包括介於碳原子之間的至少一個S、N、O或P原子，且可包括至多達約10個S、N、O或P雜原子。「介於碳原子之間」一詞意指雜原子並非諸如羥基、羰基、羧基、醛(-CHO)之端基的一部分；介於碳原子之間基團包括但
不侷限於醚、硫醚、酯、硫酯、及胺基。該等雜原子可全為一種種類，例如全為O原子，或者可為S、N、O及P中之某些或全部的混合物。特別是，該等雜原子可以一或多種醚、硫醚、酯、硫酯，或胺基之一部分的形式存在。
在特定具體實例中，式I之化合物具有下式
在其他具體實例中，式I之化合物具有下式
其中R1於各次出現時可獨立為烷基或R3。
更明確地說，在式I之化合物中，R3可為
其中R7為C1-20烴基、C1-20烴氧基、C1-20硫醚、C1-20烴基羰氧基或氰基；及b為0、1或2。
R5可為嗎啉基或吡咯啶基，且特別的是，R5可選自
在特定具體實例中，R3可為-O(CH2CH2O)mCH2CH2NR6；且m為0或0至約20之整數，或R3可選自
在本發明範例化合物中，--R1為C8H17且R3係選自：
--R1為且R3係選自
--R1為C8H17，且R3為；--R1為C8H17，且R3為；--R1為C8H17，且R3為；--R1為C8H17，且R3為；--R1為，且R3為；--R1為，且R3為；--R1為，且R3為；--R1為，且R3為。
在另一實施樣態中，本發明有關包括以下之光電裝置陰極；陽極；置於該陰極與陽極之間之電致發光層；及置於該電致發光層與該陰極之間且包含式Ia之化合物的層。
式Ia之化合物所包含之種類包括式I之化合物。
在某些具體實例中，式Ia之化合物為
而在其他具體實例中，式Ia之化合物為
在另外之具體實例中，該光電裝置包括式Ia之化合物，其中R3a為含有至少一個醚、硫醚、酯、硫酯或烷基胺基之C1-20烴基。
適用之寡聚物阻擋層的某些實例係呈現於表2。
式I之化合物通常為非晶形材料，其可藉由從適用的有機溶劑蒸發鑄製而鑄塑成薄膜。只要茀寡聚物長度不超過約3個茀段，該等寡聚物之三重態能量高於大部分發光性主體材料且可發生三重態阻擋。
式I之化合物可以容易地藉由典型芳基偶合反應(諸如鈴木(Suzuki)或山本(Yamamoto)偶合作用)製備。
特別是，該等化合物可藉由鈴木交叉偶合反應製備。鈴木交叉偶合反應之大致製程包括在適用溶劑中於鹼及Pd觸媒之存在下混合芳基鹵化物與芳基硼酸鹽(或硼酸)，且在惰性氣氛中加熱。適用溶劑包括但不侷限於二烷、THF、乙醇、甲苯及其混合物。範例鹼類包括Na2CO3、K2CO3、Cs2CO3、磷酸鉀及其水合物。可以固態粉末或水溶液形式將該等鹼類添加於該反應中。適用之觸媒包括增添第二配位基之Pd(PPh3)4、Pd(OAc)2及Pd(dba)2。範例配位基包括以下所示之二烷基膦聯苯配位基，其中Cy為環己基。
在最簡單之實例中，光電裝置包括陽極層及對應之陰極層，電致發光層配置於該陽極與陰極之間。當施加偏電壓通過該等電極時，電子由該陰極注射至該電致發光層內，同時電子係從陽極自電致發光層移除(或「電洞」係從陽極「注射」至該電致發光層內)。就有機發光裝置(OLED)而言，當電洞與電子在該電致發光層內組合以形成單態或三重態激子時產生發光現象，發光現象係於單態及/或三重態激子經由輻射衰變衰變成其基態時發生。就光伏打(PV)裝置而言，吸光作用形成電流流動。
除陽極、陰極及發光材料以外可存在光電裝置中之其他組件包括電洞注射層、電子注射層及電子傳輸層。該電子傳輸層不一定與陰極直接接觸，且該電子傳輸層亦經常
作為電洞阻擋層以防止電洞朝向陰極遷移。可存在有機發光裝置中之額外組件包括電洞傳輸層、電洞傳輸發光層及電子傳輸發光層。
該有機電致發光層(即，該發光層)係在有機發光裝置中之層，當操作時其含有相當高濃度之電子與電洞二者，且提供激子形成與發光之位置。電洞注射層係與陽極接觸之層，其促使電洞從陽極注射至該OLED之內層內；且電子注射層係與陰極接觸之層，其促使電子從陰極注射至該OLED內；電子傳輸層係促使電子從陰極或電子注射層傳導至電荷重組合位置之層。在包含電子傳輸層之有機發光裝置操作期間，存在該電子傳輸層中之電荷載子(即電洞與電子)大部分為電子，且可經由存在該發光層中之電洞與電子重組合而發光。電洞傳輸層係在OLED於操作狀態下時促使電洞從陽極及/或電洞注射層傳導至電荷重組合位置之層，且其不一定與該陽極直接接觸。電洞傳輸發光層係在OLED於操作狀態時促使電洞傳導至電荷重組合位置之層，其中大部分電荷載子為電洞，且其中不僅經由與殘留電子重組合而發光，亦經由能量從電荷重組合區轉移至該裝置中其他處而發光。電子傳輸發光層係在OLED於操作狀態時促使電子傳導至電荷重組合位置之層，其中大部分電荷載子為電洞，且其中不僅經由與殘留電洞重組合而發光，亦經由能量從電荷重組合區轉移至該裝置中其他處而發光。
適於用作陽極之材料包括體電阻係數(bulk resistivity
)較佳為每平方約1000歐姆之材料，其係藉由四點探針技術測得。由於氧化銦錫(ITO)對光傳輸而言實質上為透明因此促使從電活性有機層發出之光逸出，故其經常用作陽極。可用作陽極層之其他材料包括氧化錫、氧化銦、氧化鋅、氧化銦鋅、氧化鋅銦錫、氧化銻、及其混合物。
適於作為陰極之材料包括一般導電體，其包括但不侷限於可注射負電荷載子(電子)至OLED之內層內之金屬。亦可使用諸如ITO之金屬氧化物。適於用作陰極之金屬包括K、Li、Na、Cs、Mg、Ca、Sr、Ba、Al、Ag、Au、In、Sn、Zn、Zr、Sc、Y、鑭系元素、其合金及其混合物。用作陰極層之適用合金材料包括Ag-Mg、Al-Li、In-Mg、Al-Ca及Al-Au合金。層狀非合金結構亦可用於陰極，諸如金屬(諸如鈣)或金屬氟化物(諸如LiF)之薄層，其係以較厚金屬(諸如鋁或銀)層覆蓋。特別是，陰極可由單一金屬，尤其是鋁金屬所構成。
式I之化合物可用於電子傳輸層以代替傳統材料或與傳統材料一起使用，所述傳統材料是諸如聚(9,9-二辛基茀)、三(8-羥基喹啉)鋁(Alq3)、2,9-二甲基-4,7-二苯基-1,1-啡啉、4,7-二苯基-1,10-啡啉、2-(4-聯苯基)-5-(4-第三丁基苯基)-1,3,4-二唑、3-(4-聯苯基)-4-苯基-5-(4-第三丁基苯基)-1,2,4-三唑、含1,3,4-二唑之聚合物、含1,3,4-三唑之聚合物、含喹啉之聚合物及氰基-PPV。
適用於電洞傳輸層之材料包括如美國專利第6,023,371
號中所揭示之1,1-雙((二-4-甲苯胺基)苯基)環己烷、N,N'-雙(4-甲基苯基)-N,N'-雙(4-乙基苯基)-(1,1'-(3,3'-二甲基)聯苯)-4,4'-二胺、四-(3-甲基苯基)-N,N,N',N'-2,5-苯二胺、苯基-4-N,N-二苯胺基苯乙烯、對(二乙胺基)苯甲醛二苯基腙、三苯胺、1-苯基-3-(對(二乙胺基)苯乙烯基)-5-(對(二乙胺基)苯基)吡唑啉、1,2-反式-雙(9H-咔唑-9-基)環丁烷、N,N,N',N'-四(4-甲基苯基)-(1,1'-聯苯)-4,4'-二胺、銅酞青、聚乙烯基咔唑、(苯甲基)聚矽烷；聚(3,4-伸乙二氧基噻吩)(PEDOT)、聚苯胺、聚乙烯基咔唑、三芳基二胺、四苯基二胺、芳族三級胺類、腙衍生物、咔唑衍生物、三唑衍生物、咪唑衍生物、具有胺基之二唑衍生物及聚噻吩類。
適用於發光層之材料包括電致發光聚合物，諸如聚茀類，較佳為聚(9,9-二辛基茀)及其共聚物，諸如聚(9,9'-二辛基茀-共聚-雙-N,N'-(4-丁基苯基)二苯胺)(F8-TFB)；聚(乙烯基咔唑)及聚伸苯基乙烯及其衍生物。此外，該發光層可包括藍色、黃色、橙色、綠色或紅色磷光染料或金屬錯合物，或其組合。適於用作磷光染料之材料包括但不侷限於三(1-苯基異喹啉)銥(III)(紅色染料)、三(2-苯基吡啶)銥(綠色染料)及銥(III)雙(2-(4,6-二茀苯基)吡啶-N,C2)(藍色染料)。亦可使用得自ADS(American Dyes Source,Inc.)之市售電致螢光(electrofluorescent)及電致磷光(electrophosphorescent
)金屬錯合物。ADS綠色染料包括ADS060GE、ADS061GE、ADS063GE及ADS066GE、ADS078GE及ADS090GE。ADS藍色染料包括ADS064BE、ADS065BE及ADS070BE。ADS紅色染料包括ADS067RE、ADS068RE、ADS069RE、ADS075RE、ADS076RE、ADS067RE及ADS077RE。
本文所使用之烴基意指除非另外指定否則僅含有氫與碳之有機基團，且可包括芳族、脂族、環脂族以及含有脂族、環脂族及芳族基團中之二或多者的基團。
如本文所使用，烷基希望包括直鏈、分支或環狀烴結構及其組合，包括低碳數烷基及高碳數烷基。較佳之烷基為C20或更低碳數者。低碳數烷基係指具有1至6個碳原子(較佳為1至4個碳原子)之烷基，且包括甲基、乙基、正丙基、異丙基及正丁基、第二丁基及第三丁基。高碳數烷基係指具有7或更多個碳原子(較佳為7至20個碳原子)之烷基，且包括正庚基、第二庚基及第三庚基、辛基及十二基。環烷基係烷基之子組，且包括具有3至8個碳原子之環狀烴基。環烷基之實例包括環丙基、環丁基、環戊基及降莰基。烯基與炔基係指其中二或多個氫原子分別經雙鍵或三鍵替代的烷基。
芳基及雜芳基意指含有0至3個選自氮、氧或硫之雜原子的5-或6-員芳環或雜芳環；含有0至3個選自氮、氧或硫之雜原子的雙環9-或10-員芳環或雜芳環系統；或含有0至3
個選自氮、氧或硫之雜原子的三環13-或14-員芳環或雜芳環系統。芳族6-至14-員碳環包括例如苯、萘、二氫化茚、四氫萘及茀；5-至10-員芳族雜環包括例如咪唑、吡啶、吲哚、噻吩、苯並哌喃酮、噻唑、呋喃、苯並咪唑、喹啉、異喹啉、喹啉、嘧啶、吡、四唑及吡唑。
芳基烷基意指附接於芳基環之烷基殘基。實例為苯甲基及苯乙基。雜芳基烷基意指附接於雜芳環上之烷基殘基。實例包括吡啶基甲基及嘧啶基乙基。烷基芳基意指附接有一或多個烷基之芳基殘基。實例為甲苯基及基。
烷氧基係指經由氧而附接於母結構之具有1至8個碳原子的直鏈、分支、環狀構造及其組合。實例包括甲氧基、乙氧基、丙氧基、異丙氧基、環丙氧基及環己氧基。低碳數烷氧基係指含有一至四個碳之基團。
醯基係指經由羰基官能基附接於母結構之具有1至8個碳原子的直鏈、分支、環狀構造，為飽和、不飽和與芳族及其組合。只要附接於母體之點仍在該羰基，醯基殘基中之一或多個碳可經氮、氧或硫替代。實例包括乙醯基、苯甲醯基、丙醯基、異丁醯基、第三丁氧羰基、及苯甲氧羰基。低碳數醯基係指含有一至四個碳之基團。
雜環意指其中之一至兩個碳係經雜原子(諸如氧、氮或硫)替代之環烷基或芳基殘基。在本發明範圍內之雜環實例包括吡咯啶、吡唑、吡咯、吲哚、喹啉、異喹啉、四氫異喹啉、苯並呋喃、苯並二烷、苯並二唑(當作為取代基出現時通稱為亞甲基二氧基苯)、四唑、嗎啉、噻
唑、吡啶、嗒、嘧啶、噻吩、呋喃、唑、唑啉、異唑、二烷及四氫呋喃。
經取代的基團係指包括但不侷限於烷基、烷基芳基、芳基、芳基烷基及雜芳基之殘基，且其中該殘基之至多3個H原子係經低碳數烷基、經取代烷基、烯基、經取代烯基、芳基、經取代芳基、鹵代烷基、烷氧基、羰基、羧基、羧烷氧基、羧醯胺基、醯氧基、甲脒基、硝基、鹵基、羥基、OCH(COOH)2、氰基、一級胺基、二級胺基、醯基胺基、烷硫基、亞碸、碸、苯基、苯甲基、苯氧基、苯甲氧基、雜芳基或雜芳氧基替代。
鹵代烷基係指烷基殘基，其中一或多個H原子係經鹵素原子替代；鹵代烷基一詞包括全鹵代烷基。在本發明範圍內之鹵代烷基實例包括CH2F、CHF2及CF3。
本文所述許多化合物可含有一或多個不對稱中心，且因此可產生鏡像異構物、非鏡像異構物、及可以絕對立體化學之術語界定為(R)-或(S)-之其他立體異構形式。本發明意欲包括所有可能之異構物以及其消旋與光學純質形式。光學活性(R)-及(S)-異構物可使用手性合成組元或手性反應物製備，或使用慣用技術分析。當本文所述之化合物含有烯烴雙鍵或其他幾何不對稱中心時，除非另外指定，否則希望該等化合物包括E與Z幾何異構物二者。同樣地，亦希望包括所有互變異構形式。
氧雜烷基係指其中一或多個碳已經氧替代之烷基殘基。其係經由烷基殘基附接於母結構。實例包括甲氧基丙氧
基、3,6,9-三氧雜癸基等。氧雜烷基一詞的定義係為先前技術中所理解之定義(詳見Naming and Indexing of Chemical Substances for Chemical Abstracts，由American Chemical Society出版，¶196，但不受¶127(a)限制)，即，其係指其中之氧係經由單鍵與其相鄰原子鍵結(形成醚鍵)之化合物；其非指羰基中發現之雙鍵鍵結之氧。類似地，硫雜烷基及氮雜烷基係指其中一或多個碳已分別經硫或氮替代之烷基殘基。實例包括乙胺基乙基及甲硫基丙基。
矽基意指其中一至三個碳係經四價矽替代且經由矽原子附接於母結構之烷基殘基。矽氧基係其中兩個碳均被以烷基殘基、芳基殘基或環烷基殘基封端之四價矽替代且經由氧原子附接於母結構的烷氧基殘基。
如本文所使用，「芳族基」一詞係指包含至少一個芳族基團之具有至少一價之原子陣列。該包含至少一個芳族基團之具有至少一價之原子陣列可包括諸如氮、硫、硒、矽及氧之雜原子，或可僅由碳與氫所組成。如本文所使用，「芳族基」一詞包括但不侷限於苯基、吡啶基、呋喃基、噻吩基、萘基、伸苯基及聯苯基。如所述，芳族基含有至少一個芳族基團。該芳族基團一定為具有4n+2「未定域」電子之環狀結構，其中「n」係等於1或更大之整數，以苯基(n=1)、噻吩基(n=1)、呋喃基(n=1)、萘基(n=2)、薁基(n=2)、蒽基(n=3)等做說明。該芳族基亦可包括非芳族組分。例如，苯甲基係包含苯環(芳族基
團)及亞甲基(非芳族組分)之芳族基。類似地，四氫萘基係包含與非芳族組分-(CH2)4-稠合之芳族基團(C6H3)的芳族基。為求便利起見，本文中將「芳族基」一詞界定為帶有廣範圍的官能基，諸如烷基、烯基、炔基、鹵代烷基、鹵代芳族基團、共軛二烯基、醇基、醚基、醛基、酮基、羧酸基、醯基(例如羧酸衍生物，諸如酯類及醯胺類)、胺基、硝基等。例如，4-甲基苯基係包含甲基之C7芳族基，該甲基係是為烷基之官能基。類似地，2-硝基苯基係包含硝基之C6芳族基，該硝基為官能基。芳族基包括鹵代芳族基，諸如4-三氟甲基苯基、六氟亞異丙基雙(4-苯-1-基氧基)(即，-OPhC(CF3)2PhO-)、4-氯甲基苯-1-基、3-三氟乙烯基-2-噻吩基、3-三氯甲基苯-1-基(即，3-CCl3Ph-)、4-(3-溴丙-1-基)苯-1-基(即，4-BrCH2CH2CH2Ph-)等。芳族基之其他實例包括4-烯丙氧基苯-1-氧基、4-胺基苯-1-基(即，4-H2NPh-)、3-胺基羰基苯-1-基(即，NH2COPh-)、4-苯甲醯基苯-1-基、二氰亞甲基雙(4-苯-1-基氧基)(即，-OPhC(CN)2PhO-)、3-甲基苯-1-基、亞甲基雙(4-苯-1-基氧基)(即，-OPhCH2PhO-)、2-乙基苯-1-基、苯基乙烯基、3-甲醯基-2-噻吩基、2-己基-5-呋喃基、六亞甲基-1,6-雙(4-苯-1-基氧基)(即，-OPh(CH2)6PhO-)、4-羥甲基苯-1-基(即，4-HOCH2Ph-)、4-巰甲基苯-1-基(即，4-HSCH2Ph-)、4-甲硫基苯-1-基(即，4-CH3SPh-)、3-甲氧基苯-1-基、2-甲氧基羰基苯-1-基氧基)(例如甲基柳基)、2-硝基甲基苯-1-基(
即，2-NO2CH2Ph)、3-三甲矽基苯-1-基、4-第三丁基二甲矽基苯-1-基、4-乙烯基苯-1-基、亞乙烯基雙(苯基)等。「C3-C10芳族基」一詞包括含有至少3個但不多於10個碳原子之芳族基。芳族1-咪唑基(C3H2N2-)代表C3芳族基。苯甲基(C7H7-)代表C7芳族基。
本文所使用之「環脂族基」係指具有至少一價之基，且包含為環狀但非芳族之原子陣列。本文所界定之「環脂族基」不含有芳族基團。「環脂族基」可包含一或多個非環狀組分。例如環己基甲基(C6H11CH2-)係包含環己基環(其係環狀陣列但非芳族)與亞甲基(非環狀組分)之環脂族基。環脂族基可包括諸如氮、硫、硒、矽及氧之雜原子，或可僅由碳與氫所組成。為求便利起見，本文中將「環脂族基」一詞界定為帶有廣範圍的官能基，諸如烷基、烯基、炔基、鹵代烷基、共軛二烯基、醇基、醚基、醛基、酮基、羧酸基、醯基(例如羧酸衍生物，諸如酯類及醯胺類)、胺基、硝基等。例如，4-甲基環戊-1-基係包含甲基之C6環脂族基，該甲基係是為烷基之官能基。類似地，2-硝基環丁-1-基係包含硝基之C4環脂族基，該硝基為官能基。環脂族基可包含一或多個鹵素原子，彼等可相同或不同。鹵素原子包括例如氟、氯、溴及碘。包含一或多個鹵素原子之環脂族基包括2-三氟甲基環己-1-基、4-溴二氟甲基環辛-1-基、2-氯二氟甲基環己-1-基、六氟亞異丙基-2,2-雙(環己-4-基)(即，-C6H10C(CF3)2C6H10-)、2-氯甲基環己-1-基、3-二氟亞甲基環己-1-基、4-三氯甲基環
己-1-基氧基)、4-溴二氯甲基環己-1-基硫基、2-溴乙基環戊-1-基、2-溴丙基環己-1-基氧基(例如CH3CHBrCH2C6H10O-)等。環脂族基之其他實例包括4-烯丙氧基環己-1-基、4-胺基環己-1-基(即，H2NC6H10-)、4-胺基羰基環戊-1-基(即，NH2COC5H8-)、4-乙醯氧環己-1-基、2,2-二氰亞異丙基雙(環己-4-基氧基)(即，-OC6H10C(CN)2C6H10O-)、3-甲基環己-1-基、亞甲基雙(環己-4-基氧基)(即，-OC6H10CH2C6H10O-)、1-乙基環丁-1-基、環丙基乙烯基、3-甲醯基-2-四氫呋喃基、2-己基-5-四氫呋喃基、六亞甲基-1,6-雙(環己-4-基氧基)(即，-OC6H10(CH2)6C6H10O-)、4-羥甲基環己-1-基(即，4-HOCH2C6H10-)、4-巰甲基環己-1-基(即，4-HSCH2C6H10-)、4-甲硫環己-1-基(即，4-CH3SC6H10-)、4-甲氧基環己-1-基、2-甲氧基羰基環己-1-基氧基(2-CH3OCOC6H10O-)、4-硝基甲基環己-1-基(即，NO2CH2C6H10-)、3-三甲矽基環己-1-基、2-第三丁基二甲矽基環戊-1-基、4-三甲氧基矽基乙基環己-1-基(例如(CH3O)3SiCH2CH2C6H10-)、4-乙烯基環己烯-1-基、亞乙烯基雙(環己基)等。「C3-C10環脂族基」一詞包括含有至少3個但不多於10個碳原子之環脂族基。環脂族基2-四氫呋喃基(C4H7O-)代表C4環脂族基。環己基甲基(C6H11CH2-)代表C7環脂族基。
本文所使用之「脂族基」係指由非環狀之直鏈或分支原子陣列所組成的具有至少一價之有機基。脂族基係界定
為帶有至少一個碳原子。包含脂族基之原子陣列可包括諸如氮、硫、矽、硒及氧之雜原子，或可僅由碳與氫所組成。為求便利起見，本文將「脂族基」界定為，當作為該「非環狀之直鏈或分支原子限制」之一部分時，包括經廣範圍官能基取代之有機基，該等官能基係諸如烷基、烯基、炔基、鹵代烷基、共軛二烯基、醇基、醚基、醛基、酮基、羧酸基、醯基(例如羧酸衍生物，諸如酯類及醯胺類)、胺基、硝基。例如，4-甲基苯-1-基係包含甲基之C6脂族基，該甲基係是為烷基之官能基。類似地，4-硝基丁-1-基係包含硝基之C4脂族基，該硝基為官能基。脂族基可為包含一或多個鹵素原子之鹵代烷基，該等鹵素原子可相同或不同。鹵素原子包括例如氟、氯、溴及碘。包含一或多個鹵素原子之脂族基包括鹵化烷基：三氟甲基、溴二氟甲基、氯二氟甲基、六氟亞異丙基、氯甲基、二氟亞乙烯基、三氯甲基、溴二氯甲基、溴乙基、2-溴三亞甲基(例如-CH2CHBrCH2-)等。脂族基之其他實例包括烯丙基、胺基羰基(即，-CONH2)、羰基、2,2-二氰亞異丙基(即，-CH2C(CN)2CH2-)、甲基(即，-CH3)、亞甲基(即，-CH2-)、乙基、伸乙基、甲醯基(即，-CHO)、己基、六亞甲基、羥甲基(即，-CH2OH)、巰甲基(即，-CH2SH)、甲硫基(即，-SCH3)、甲硫基甲基(即，-CH2SCH3)、甲氧基、甲氧基羰基(即，CH3OCO-)、硝基甲基(即，-CH2NO2)、硫羰基、三甲矽基(即，(CH3)3Si-)、第三丁基二甲矽基、3-三甲氧基矽基丙基(
即，(CH3O)3SiCH2CH2CH2-)、乙烯基、亞乙烯基等。其他實例中，C1-C10脂族基含有至少一個但不多於10個碳原子。甲基(即，CH3-)係C1脂族基之實例。癸基(即，CH3(CH2)9-)係C10脂族基之實例。
寡聚茀類之大致製程係以392-59的合成為例說明：在裝配有冷凝器、氣體入口管及鐵弗龍(Teflon)磁攪拌棒之200ml的2頸燒瓶中裝入2.028g(3.00mmol)之9,9-雙-(4-己氧基苯基)-2,7-二溴茀、3.132g(6.24mmol)之9,9-二辛基-2-伸乙二氧基硼烷、0.129g(0.32mmol)之二環己基-2-(2',6'-二-甲氧基苯基)苯膦及60ml之甲苯。以氬對該溶液除氣15分鐘，然後加入0.20g(0.09mmol)之乙酸鈀，接著加入2.2g(15mmol)氫氧化四乙銨於22g水中之經除氣的溶液。將該溶液浸於70℃油浴且在氮氣覆蓋下攪拌16小時。以50ml甲苯及25ml水稀釋該經冷卻之混合物，經由矽藻土墊過濾之，且將之轉移至分液漏斗。將水相丟棄，且依序以水(2×100ml)及鹽水(1×100ml)清洗，接著使之通過含燥石膏(Drierite)的錐形器。在室溫下將該溶液與~25mg之氫硼化鈉攪拌，然後在真空下予以濃縮，且在120g矽膠上以0至30%乙酸乙酯/己烷洗提來層析殘留之油，提供2.3g之無色油：1H nmr(CDCl3)δ 8.0-7.3(m，20，茀-H)，7.3-6.8(AB四重線，8，酚醚
Ar-H)，3.96(t，4，ArOCH2)，2.04(t，8，C9-CH2)及1.8-0.6ppm(m，60，辛基-H)。
本發明之材料可溶於一般醇類，諸如1-丁醇及1-己醇。例如，本發明人已發現諸如JC392-59及392-38可容易以濃度約10mg/ml溶解於1-己醇及1-丁醇。冷卻至室溫之後，可經由從溶液直接旋轉鑄塑而將該材料沉積於不被醇溶劑溶解之聚茀聚合物層上。本發明人已發現以~1000rpm將~10mg/ml之醇溶液旋塗於塗覆聚茀之玻璃載片上形成厚度為~20nm之額外膜，本發明人將之指定為三聚體型材料之額外層。本發明人已發現可能在形成該雙層結構之後經由機械與光學二者測量在玻璃上之該聚合物膜厚度。機械測量係藉由先使用銳利邊緣刮磨該膜，然後使用表面測平儀(在此情況，使用Tencor P1)測量介於該膜頂部與玻璃之間的距離來進行。利用聚茀材料在~390nm展現其光吸收峰值且在~357nm的光吸收遠遠較低之性質來進行光學測量(本發明之許多三聚體種類在此處均有吸收峰)。因此可以藉由層吸收值將混合的吸收值拆解成二個組份，其中之一對應於聚茀，另一者對應於本發明之寡聚物。由於光吸收性(單元為OD)與平均厚度呈線性相關，此對雙層結構的存在提供額外的支持。
可能使用該等材料之有利溶解性質製造OLED裝置。為了製造該裝置，可藉由旋塗於清潔、經UV-臭氧處理之2.5cm×2.5cm之經ITO圖案化的玻璃基板上製備厚度為約60nm之PEDOT/PSS(Baytron P VP 8000，聚(3,4-伸乙基二氧噻吩)-聚(苯乙烯磺酸酯)，從HC Starck,Inc.獲得，呈溶液狀)或其他電洞注射材料的層。然後可在加熱板上於空氣中以160℃烘烤該經塗覆之基板30分鐘。可經由旋塗在該塗覆PEDOT/PSS之基板上面沉積厚度為約10至20nm之F8-TFB(得自Sumation,Inc.之辛基茀-三芳基胺共聚物)電洞傳輸層。然後可在加熱板上於氬氣中以160℃烘烤該塗覆F8-TFB-PEDOT/PSS之基板30分鐘。然後可將一層由非醇溶性聚茀材料(得自Sumation chemical或American Dye Source)組成之層溶解於諸如二甲苯之溶劑中，且將溶液沉積於該F8-TFB層上面作為發光層。該發光層之厚度至多可達200nm，但以5nm至40nm之厚度為佳。可從醇(例如1-丁醇、1-己醇)溶液沉積該三聚體材料之最終層，較佳厚度在10nm至50nm之範圍。
然後將該經塗覆基板置入鐘形罩蒸發器，且泵抽該系統直到獲得約1×10-6托之壓力為止。然後可藉由物理氣相沉積在該經塗覆基板之最終層上面沉積約7nm厚(經由經校正石英晶體微量天平測得)之氟化鈉層。然後，可藉由在真空中蒸氣沉積在該氟化鈉層上面沉積約130nm厚之鋁金屬層，以形成該OLED之陰極組件。
雖然本文僅舉例並說明本發明特定特徵，但熟悉本技
術之人士會發現許多修改與變化。因此，應暸解附錄主張權項希望將所有此等修改與變化涵括在本發明真正精神內。
Claims (3)
- 一種式I之化合物
- 一種光電裝置，其包含如申請專利範圍第1項之化合物。
- 一種光電裝置，其包含陰極；陽極；置於該陰極與陽極之間之電致發光層；及置於該電致發光層與該陰極之間的層，且該層包含如申請專利範圍第1項之化合物。
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| WO (1) | WO2011002532A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB2487207B (en) | 2011-01-12 | 2013-07-31 | Cambridge Display Tech Ltd | Electroluminescence |
| WO2013090610A1 (en) * | 2011-12-13 | 2013-06-20 | The Regents Of The University Of California | Bulk polymer composites |
| JP5841853B2 (ja) * | 2012-02-03 | 2016-01-13 | リンテック株式会社 | 導電性積層体、及び有機薄型太陽電池素子 |
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- 2009-06-29 US US12/493,781 patent/US20100327735A1/en not_active Abandoned
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2010
- 2010-03-01 WO PCT/US2010/025718 patent/WO2011002532A1/en active Application Filing
- 2010-03-01 CN CN201080030202.0A patent/CN102471678B/zh not_active Expired - Fee Related
- 2010-03-01 KR KR1020127002428A patent/KR101537437B1/ko not_active IP Right Cessation
- 2010-03-01 JP JP2012517511A patent/JP2012532101A/ja not_active Withdrawn
- 2010-03-01 EP EP10707404A patent/EP2449053A1/en not_active Withdrawn
- 2010-06-15 TW TW099119505A patent/TWI507377B/zh not_active IP Right Cessation
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2013
- 2013-05-20 US US13/897,653 patent/US20130248840A1/en not_active Abandoned
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| JP2004277368A (ja) * | 2003-03-18 | 2004-10-07 | Mitsui Chemicals Inc | フルオレン化合物、および該フルオレン化合物を含有する有機電界発光素子 |
| US20050236977A1 (en) * | 2004-04-12 | 2005-10-27 | Canon Kabushiki Kaisha | Fluorene compound and organic light-emitting device using same |
| WO2008147110A2 (en) * | 2007-05-28 | 2008-12-04 | Cheil Industries Inc. | Material for organic electro-optical device having fluorene derivative compound and organic electro-optical device including the same |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011002532A1 (en) | 2011-01-06 |
| EP2449053A1 (en) | 2012-05-09 |
| TW201127780A (en) | 2011-08-16 |
| US20130248840A1 (en) | 2013-09-26 |
| CN102471678A (zh) | 2012-05-23 |
| JP2012532101A (ja) | 2012-12-13 |
| KR101537437B1 (ko) | 2015-07-16 |
| US20100327735A1 (en) | 2010-12-30 |
| KR20120039676A (ko) | 2012-04-25 |
| CN102471678B (zh) | 2015-09-09 |
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