JP2008545630A - 有機電子素子のための化合物 - Google Patents
有機電子素子のための化合物 Download PDFInfo
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- JP2008545630A JP2008545630A JP2008511579A JP2008511579A JP2008545630A JP 2008545630 A JP2008545630 A JP 2008545630A JP 2008511579 A JP2008511579 A JP 2008511579A JP 2008511579 A JP2008511579 A JP 2008511579A JP 2008545630 A JP2008545630 A JP 2008545630A
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- -1 C═O Chemical compound 0.000 claims description 49
- 238000002347 injection Methods 0.000 claims description 31
- 239000007924 injection Substances 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 16
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 12
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- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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- 239000002019 doping agent Substances 0.000 abstract description 10
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
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- 238000002360 preparation method Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- NSRBXXWZFGGDPX-UHFFFAOYSA-N 2,8-dibromo-6,6,12,12-tetramethylindeno[1,2-b]fluorene Chemical compound C1=C2C3=CC=C(Br)C=C3C(C)(C)C2=CC2=C1C(C)(C)C1=CC(Br)=CC=C12 NSRBXXWZFGGDPX-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
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- 230000008021 deposition Effects 0.000 description 8
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- 238000010561 standard procedure Methods 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 6
- 238000001194 electroluminescence spectrum Methods 0.000 description 6
- IFYXDUXOWSLKPL-UHFFFAOYSA-N indeno[2,1-a]fluorene-5,11-dione Chemical compound C1=C2C(C=3C(=CC(C4=C5C=CC=CC5=CC=34)=O)C2=CC=C1)=O IFYXDUXOWSLKPL-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
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- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- MTUBTKOZCCGPSU-UHFFFAOYSA-N 2-n-naphthalen-1-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 MTUBTKOZCCGPSU-UHFFFAOYSA-N 0.000 description 5
- VMDDQHKTCPOZNM-UHFFFAOYSA-N 6,6,12,12-tetramethylindeno[1,2-b]fluorene Chemical compound C12=CC=CC=C2C(C)(C)C2=C1C=C1C(C)(C)C3=CC=CC=C3C1=C2 VMDDQHKTCPOZNM-UHFFFAOYSA-N 0.000 description 5
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- ADUFDSSCDCLUFT-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 ADUFDSSCDCLUFT-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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- BGZHOUYGJXZNAI-UHFFFAOYSA-N 2-N,2-N,2-N',2-N',7-N,7-N,7-N',7-N'-octakis-phenyl-1,1'-spirobi[fluorene]-2,2',7,7'-tetramine Chemical compound C12=CC=C(N(C=3C=CC=CC=3)C=3C=CC=CC=3)C=C2C=C(C23C(=CC=C4C5=CC=C(C=C5C=C43)N(C=3C=CC=CC=3)C=3C=CC=CC=3)N(C=3C=CC=CC=3)C=3C=CC=CC=3)C1=CC=C2N(C=1C=CC=CC=1)C1=CC=CC=C1 BGZHOUYGJXZNAI-UHFFFAOYSA-N 0.000 description 3
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- 230000002411 adverse Effects 0.000 description 3
- OCHLUUFRAVAYIM-UHFFFAOYSA-N bis(9,9'-spirobi[fluorene]-2-yl)methanone Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C1=C2)C3=CC=CC=C3C1=CC=C2C(=O)C1=CC=C(C=2C(=CC=CC=2)C23C4=CC=CC=C4C4=CC=CC=C43)C2=C1 OCHLUUFRAVAYIM-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 239000012044 organic layer Substances 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
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- 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 2
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
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- UBCKKCHYZANYJV-UHFFFAOYSA-N 5,5,15,15,25,25-hexamethylheptacyclo[14.11.0.02,14.04,12.06,11.018,26.019,24]heptacosa-1(16),2(14),3,6,8,10,12,17,19,21,23,26-dodecaene Chemical compound C12=CC=CC=C2C(C)(C)C2=C1C=C(C(C=1C=C3C4=CC=CC=C4C(C3=CC=11)(C)C)(C)C)C1=C2 UBCKKCHYZANYJV-UHFFFAOYSA-N 0.000 description 2
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 239000003086 colorant Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- MCRSZLVSRGTMIH-UHFFFAOYSA-N ditert-butyl(chloro)phosphane Chemical compound CC(C)(C)P(Cl)C(C)(C)C MCRSZLVSRGTMIH-UHFFFAOYSA-N 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
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- 238000007645 offset printing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 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 1
- 244000045947 parasite Species 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
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 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 1
- 239000012071 phase Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 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
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
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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
- H10K85/60—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
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- C07D215/38—Nitrogen atoms
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- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
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Abstract
【化1】
Description
1.効率は、特に蛍光OLEDの場合には、未だあまりにも低く、改善する必要がある。
Y、Zは、同一であるか異なり、N、P、P=O、PF2、P=S、As、As=O、As=S、Sb、Sb=O、Sb=S、C=O、O、S、Se、Te、S=O、SO2、Se=O、SeO2、Te=O若しくはTeO2であり:
Ar1、Ar2、Ar3は、出現毎に同一であるか異なり、1以上のR1基により置換されていてもよい5〜24個の芳香族環原子を有するアリール若しくはヘテロアリール基であり;
Ar4、Ar5、Ar6、Ar7は、出現毎に同一であるか異なり、1以上のR1基により置換されていてもよい5〜40個の芳香族環原子を有する芳香族環原子を有する芳香族若しくは複素環式芳香族環構造であり;
Eは、出現毎に同一であるか異なり、単結合、N(R1)、O、S、C(R1)2、Si(R1)2、若しくはB(R1)であり;
R1は、出現毎に同一であるか異なり、H、F、Cl、Br、I、CN、NO2、B(OR2)2、Si(R2)3、1〜40個のC原子を有する直鎖アルキル、アルコキシ若しくはチオアルコキシ基、又は3〜40個のC原子を有する分岐或いは環状アルキル、アルコキシ若しくはチオアルコキシ基(夫々は1以上の置換基R2により置換されていてもよく、そして、1以上の隣接しないCH2は、-R2C=CR2-、-C≡C-、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、-O-、-S-、-CO-O若しくはCONR2で置き代えられていてもよく、また、1以上のH原子は、F、Cl、Br、I、CN若しくはNO2で置き代えられていてもよい)、又は1以上の非芳香族R1基により置換されていてもよい5〜40個の芳香族環原子を有する芳香族若しくは複素環式芳香族環構造、又は1以上の非芳香族R1基により置換されていてもよい5〜40個の芳香族環原子を有するアリールオキシ若しくはヘテロアリールオキシ基、又は、これらの構造の組み合わせであり;ここで、2以上の置換基R1は、互いにモノ若しくはポリ環状環構造を形成するものであってもよく;
R2は、出現毎に同一であるか異なり、H若しくは1〜20個のC原子を有する脂肪族又は芳香族炭化水素基であり;
X1、X4は、出現毎に同一であるか異なり、B(R1)、C(R1)2、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、S=O、SO2、N(R1)、P(R1)、P(=O)R1、P(=S)R1又はこれら基の2、3或いは4個の組み合わせから選択され、Ar1、Ar2と共に環状構造を規定するブリッジであり;
X2、X3は、出現毎に同一であるか異なり、B(R1)、C(R1)2、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、S=O、SO2、N(R1)、P(R1)、P(=O)R1、P(=S)R1又はこれら基の2、3或いは4個の組み合わせから選択され、Ar2、Ar3と共に環状構造を規定するブリッジであり
n、o、pは、出現毎に同一であるか異なり、0若しくは1であるが、但し、X1がC(R1)2ブリッジ以外の基(R1は開鎖アルキル基である)であるときにだけ、n、p、oは同時に0であってもよく(n=0かつo=0かつp=0は、ここでは、2個のH若しくはR1基がブリッジの代わりに存在することを意味する。);
q、rは、Y若しくはZ基の対応する中央の原子が第5主族からの元素であるならば、出現毎に1であり、Y若しくはZ基の対応する中央の原子が第4若しくは第6主族からの元素であるならば、出現毎に0であり;
sは、1、2若しくは3であり;
tは、出現毎に同一であるか異なり0若しくは1であり、ここでt=0は、R1基がE基の代わりに結合していることを意味し、;更に、q=0ならばt=0である。
も好ましい。これら化合物は、特に好ましくは、380nm〜750nm間に合計で複数の最大発光長を有し、全体として、白色発光が生じる、即ち、式(1)の化合物に加えて、蛍光発光若しくは燐光発光し得、黄色、オレンジ色若しくは赤色光を発光する少なくとも一つの更なる発光化合物も使用される。特に好ましいものは、3層構造であり、これら層の少なくとも一つの層は式(1)の化合物を含み、その層は青色、緑色及びオレンジ色若しくは赤色発光するものである。(基本構造については、WO 05/011013参照。)広帯域エミッターもまた白色発光OLEDのために使用することができる。
以下の合成は、他に断らない限り、保護ガス雰囲気下で行われる。出発物質は、ALDRICH若しくはABCRから購入され得る。(パラジウム(II)アセテート、ジ-tert-ブチルクロロホスフィン、アミン、無機物、溶媒)、6,12-ジヒドロ[1,2b]インデノフルオレンは、Hadizad et al., Org.Lett.2005,7(5),795-797,の方法により調製され、[1,2b]インデノフルオレン-6,12-ジオンは、Deuschei et al.,Helv.Chimica Acta 1951,34,2403の方法により調製され、2-ブロモ-4,4’-ジ-tert-ブチルビフェニルは、Tashiro et al.,J.Org.Chem.1979,44(17),3037の方法により調製され、1,4-ジブロモ-2,5-ジヨードベンゼンは、Chanteau et al., J. Org. Chem. 2003, 68(23), 8750,の方法により調製され、3,9-ジブロモ-5,11-ジメチルインドロ[3,2-b]カルバゾールは、Li et al., Adv. Mat. 2005, 17(7), 849の方法による3,9-ジブロモ-5,11-ビスドデシルインドロ[3,2-b]カルバゾールと類似の方法で調製される。
a)6,6,12,12-テトラメチル-6,12-ジヒドロインデノ[1,2b]フルオレン
a)ジスピロ[2,7-ジ-tert-ブチルフルオレン-9,6’-インデノフルオレン[1,2b]フルオレン-12’-9”-フルオレン]
a)2,8-ジブロモ[1,2b]インデノフルオレン-6,12-ジオン
a)2’,5’-ジブロモ-4,4,4’,4’-テトラ-p-トリル-[1,1’,4,4]-ターフェニル-4,4’-ジアミン
OLEDは、WO 04/058911に記載される一般的プロセスにより製造されるが、これは、夫々の状況(例えば、最適な効率と色を達成するための層の厚さの変化)に対する個々の場合において適合される。
正孔輸送層(HTM1):B2(例2による化合物)
若しくは: B1(例1による化合物)
若しくは: B9(例9による化合物)
若しくは: B15(例15による化合物)
若しくは: B37(例37による化合物)
若しくは: 比較例として、4,4’,4”-トリス(N-1-ナフチル-N-フェニルアミノ)トリフェニルアミン(NaphDATAと略称、SynTecから購入)
正孔輸送層(HTM2):20nmのNPB(N-ナフチル-N-フェニル-4,4’-ジアミノビフェニル)
発光層(EML):30nm、母体材料として9,10-ビス(1-ナフチルアントラセン)(H1と略称)、5%のトリス[4-(2,2-ジフェニルビニル)フェニルアミンをドーパントとしてドープ(D1と略称、蒸着、Wo 06/000388により合成)
電子伝導体(ETC):20nmAlQ3(SynTec社から購入したトリス(キノリナート)アルミニウム(III))
陰極:150nmのAl上の1nmLiF。
OLEDは、WO 04/093027に記載される一般的プロセスにより製造されるが、これは、夫々の状況(例えば、最適な効率と色を達成するための層の厚さの変化)に対する個々の場合において適合させられる。
正孔輸送層(HTM1):B2(例2による化合物)
若しくは: 比較例として、4,4’,4”-トリス(N-1-ナフチル-N-フェニルアミノ)トリフェニルアミン(NaphDATAと略称、SynTecから購入)(比較標準)
正孔輸送層(HTM2):20nm(蒸着、WO 99/12888により調製されたS-TAD;2,2’,7,7’-テトラキス(ジフェニルアミノ)-スピロビフルオレン)
若しくは:20nmのNPB(N-ナフチル-N-フェニル-4,4’-ジアミノビフェニル)
発光層(EML):40nm、ケトン-1(ビス(9,9’-スピロビフルオレン-2-イル)ケトン(蒸着、WO 04/093027により合成)15%トリプレットエミッターE1(WO 04/085449により合成)でドープ
AlQ3:20nm(蒸着、SynTecから購入されたAlQ3、;トリス(キノリノラート)アルミニウム(III))、
陰極:150nmのAl上の1nmLiF。
OLEDは、WO 04/093027に記載される一般的プロセスにより製造されるが、これは、夫々の状況(例えば、最適な効率と色を達成するための層の厚さの変化)に対する個々の場合において適合させられる。
正孔輸送層(HTM1):20nmの4,4’,4”-トリス(N-1-ナフチル-N-フェニルアミノ)トリフェニルアミン(NaphDATAと略称、SynTecから購入)
正孔輸送層(HTM2):20nmのS-TAD(蒸着、WO 99/12888により調製されたS-TAD;2,2’,7,7’-テトラキス(ジフェニルアミノ)-スピロビフルオレン)
発光層(EML):40nmのケトン-1(ビス(9,9’-スピロビフルオレン-2-イル)ケトン(蒸着、WO 04/093027により合成)15%トリプレットエミッターE1(WO 04/085449により合成)でドープ
電子伝導層:20nmのB19(例19による化合物)
若しくは: 20nmのB26(例26による化合物)
若しくは: 20nmのB31(例31による化合物)
若しくは: 20nmのAlQ3(SynTecから購入されたAlQ3、;トリス(キノリノラート)アルミニウム(III)比較)、
陰極:150nmのAl上の1nmLiF。
OLEDは、WO 04/093027に記載される一般的プロセスにより製造されるが、これは、夫々の状況(例えば、最適な効率と色を達成するための層の厚さの変化)に対する個々の場合において適合させられる。
正孔輸送層(HTM1):20nmの4,4’,4”-トリス(N-1-ナフチル-N-フェニルアミノ)トリフェニルアミン(NaphDATAと略称、SynTecから購入)
正孔輸送層(HTM2):20nmのS-TAD(蒸着、WO 99/12888により調製されたS-TAD;2,2’,7,7’-テトラキス(ジフェニルアミノ)-スピロビフルオレン)
発光層(EML):20nmのB19(例26による化合物)
若しくは: 20nmのB26(例31による化合物)
若しくは: 20nmのB31(例31による化合物)
若しくは: ケトン-1(ビス(9,9’-スピロビフルオレン-2-イル)ケトン(蒸着、WO 04/093027により合成)(比較標準)いずれの場合も10%トリプレットエミッターE2)(WO 05/033244により合成)でドープ
電子伝導層:20nmのAlQ3(蒸着、SynTecから購入されたAlQ3、;トリス(キノリノラート)アルミニウム(III))、
陰極:150nmのAl上の1nmLiF。
OLEDは、WO 04/058911に記載される一般的プロセスにより製造されるが、これは、夫々の状況(例えば、最適な効率と色を達成するための層の厚さの変化)に対する個々の場合において適合させられる。
正孔輸送層(HTM1):20nmのB2(例2による化合物)
正孔輸送層(HTM2):20nmのNPB(N-ナフチル-N-フェニル-4,4’-ジアミノビフェニル)
発光層(EML):B2(例2による化合物)若しくはB17(例17による化合物)をドーパントとして、x%(表参照)でドープされた母体材料としてのH1、H2若しくはH3の30nmの層
電子伝導層:20nm(蒸着、SynTecから購入されたAlQ3、;トリス(キノリノラート)アルミニウム(III))、
陰極:150nmのAl上の1nmLiF。
a)ビス(N-(4-tert-ブチルフェニル)N-フェニルアミノ)-6,6,12,12-テトラオクチル-6,12-ジヒドロインデノ[1,2b]フルオレン
a)12,15-ジヒドロ-6,6,12,12,15,15-ヘキサメチル-6H-ジインデノ[1,2-b:2’,1’-h]フルオレン
a)2,8-ビス(ビス(4-ブロモフェニル)アミノ)-6,6,12,12-テトラオクチル-6,12-ジヒドロインデノ[1,2b]フルオレン
a)2,8-ビス((4-ブロモフェニル)(4-メチルフェニル)アミノ)-6,6,12,12-テトラメチル-6,12-ジヒドロインデノ[1,2b]フルオレン
OLEDは、WO 04/058911に記載される一般的プロセスにより製造されるが、これは、夫々の状況(例えば、最適な効率と色を達成するための層の厚さの変化)に対する個々の場合において適合させられる。
正孔輸送層(HTM1):B89(例89による化合物)
若しくは: B90(例90による化合物)
若しくは: 比較例として、4,4’,4”-トリス(N-1-ナフチル-N-フェニルアミノ)トリフェニルアミン(NaphDATAと略称、SynTecから購入)
正孔輸送層(HTM2):20nmのNPB(N-ナフチル-N-フェニル-4,4’-ジアミノビフェニル)
発光層(EML):母体材料として9,10-ビス(1-ナフチルアントラセン)(H1と略称)、5%のトリス[4-(2,2-ジフェニルビニル)フェニル]アミンをドーパントとしてドープ(D1と略称、蒸着、WO 06/000388により合成)された30nmのドープ層
電子伝導(ETC):20nmAlQ3(蒸着、SynTecから購入されたトリス(キノリナート)アルミニウム(III))、
陰極:150nmのAl上の1nmLiF。
Claims (22)
- 式(1)の化合物。
Y、Zは、同一であるか異なり、N、P、P=O、PF2、P=S、As、As=O、As=S、Sb、Sb=O、Sb=S、C=O、O、S、Se、Te、S=O、SO2、Se=O、SeO2、Te=O若しくはTeO2であり;
Ar1、Ar2、Ar3は、出現毎に同一であるか異なり、1以上のR1基により置換されていてもよい、5〜24個の芳香族環原子を有するアリール若しくはヘテロアリール基;
Ar4、Ar5、Ar6、Ar7は、出現毎に同一であるか異なり、1以上のR1基により置換されていてもよい、5〜40個の芳香族環原子を有する芳香族若しくは複素環式芳香族環構造であり;
Eは、出現毎に同一であるか異なり、単結合、N(R1)、O、S、C(R1)2、Si(R1)2、若しくはB(R1)であり;
R1は、出現毎に同一であるか異なり、H、F、Cl、Br、I、CN、NO2、Si(R2)3、B(OR2)2、1〜40個のC原子を有する直鎖アルキル、アルコキシ若しくはチオアルコキシ基、又は3〜40個のC原子を有する分岐或いは環状アルキル、アルコキシ若しくはチオアルコキシ基(各鎖は1以上のR2基により置換されていてもよく、そして、1以上の隣接しないCH2基は、-R2C=CR2-、-C≡C-、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、-O-、-S-、-CO-O若しくはCONR2で置き代えられていてもよく、また、1以上のH原子は、F、Cl、Br、I、CN若しくはNO2で置き代えられていてもよい)、又は1以上の非芳香族R1基により置換されていてもよい5〜40個の芳香族環原子を有する芳香族若しくは複素環式芳香族環構造、又は1以上の非芳香族R1基により置換されていてもよい5〜40個の芳香族環原子を有するアリールオキシ若しくはヘテロアリールオキシ基、又は、これらの構造の組み合わせであり;ここで、2以上の置換基R1は、互いにモノ若しくはポリ環状環構造を形成するものであってもよく;
R2は、出現毎に同一であるか異なり、H若しくは1〜20個のC原子を有する脂肪族又は芳香族炭化水素基であり、
X1、X4は、出現毎に同一であるか異なり、C(R1)2、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、S=O、SO2、N(R1)、P(R1)、P(=O)R1、P(=S)R1、B(R1)若しくはこれら基の2、3或いは4個の組み合わせから選択され、Ar1、Ar2と共に環状構造を規定するブリッジであり;
X2、X3は、出現毎に同一であるか異なり、B(R1)、C(R1)2、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、S=O、SO2、N(R1)、P(R1)、P(=O)R1、P(=S)R1若しくはこれら基の2、3或いは4個の組み合わせから選択され、Ar2、Ar3と共に環状構造を規定するブリッジであり;
n、o、pは、出現毎に同一であるか異なり、0若しくは1であるが、但し、X1がC(R1)2ブリッジ以外の基(R1は開鎖アルキル基である)であるときにだけ、n、p及びoは同時に0であってもよく(n=0かつo=0かつp=0は、ここでは、2個のH若しくはR1基がブリッジの代わりに存在することを意味する。);
q、rは、Y若しくはZ基の対応する中央の原子が第5主族からの元素であるならば、出現毎に1であり、また、Y若しくはZ基の対応する中央の原子が第4若しくは第6主族からの元素であるならば、出現毎に0であり;
sは、1、2若しくは3であり;
tは、出現毎に同一であるか異なり、0若しくは1であり、ここでt=0は、R1基がE基の代わりに結合していることを意味し、;更に、q=0ならばt=0である。 - 記号Y、Zは、同一であるか異なり、窒素、C=O、燐若しくはP=Oであることを特徴とする請求項1記載の化合物。
- 記号Ar1、Ar2、Ar3は、出現毎に同一であるか異なり、1若しくは2個のR1基により置換されていてもよい、5〜16個の芳香族環原子を有するアリール若しくはヘテロアリール基であることを特徴とする請求項1又は2記載の化合物。
- 記号Ar4、Ar5、Ar6、Ar7は、出現毎に同一であるか異なり、夫々1以上のR1基により置換されていてもよい5〜16個の芳香族環原子を有する芳香族若しくは複素環式芳香族環構造、トリアリールアミン又はスピロビフルオレンであることを特徴とする請求項1乃至4項の何れか1項記載の化合物。
- 記号R1は、出現毎に同一であるか異なり、H、F、CN、1〜5個のC原子を有する直鎖アルキル基又は3〜5個のC原子を有する分岐アルキル基(夫々の場合、1以上の隣接しないCH2基は、-R2C=CR2-、-C≡C-、-O-若しくは-S-で置き代えられていてもよく、また、1以上のH原子は、Fで置き代えられていてもよい)又は1以上のR2基により置換されていてもよい2〜16個のC原子を有する1価アリール若しくはヘテロアリール基であり;2以上のR1基は、ここでまた互いに環構造を形成するものであってもよいことを特徴とする請求項1乃至5項の何れか1項記載の化合物。
- 記号X1、X2、X3及びX4は、出現毎に同一であるか異なり、C(R1)2、C=O、C=NR1、O、S、S=O、SO2、N(R1)、P(R1)、P(=O)R1、C(R1)2-C(R1)2、C(R1)2-C(R1)2-C(R1)2、C(R1)2-O及びC(R1)2-O-(R1)2から選択され、Ar1及びAr2と共に若しくはAr2及びAr3と共に環状構造を規定するブリッジであることを特徴とする請求項1乃至7項の何れか1項記載の化合物。
- R1基が互いに環構造を形成することを特徴とする請求項1乃至9項の何れか1項記載の化合物。
- Y=Zであることを特徴とする請求項1乃至10項の何れか1項記載の化合物。
- 構造(1)乃至(104)から選択されることを特徴とする請求項1乃至11項の何れか1項記載の化合物。
- 式(1)の化合物中の1以上のR1基はポリマー、オリゴマー若しくはデンドリマーへの結合を表す、1以上の式(1)の化合物を含む、共役、一部共役或いは非共役ポリマー、オリゴマー若しくはデンドリマー。
- ポリマーは、フルオレン、スピロビフルオレン、パラフェニレン、カルバゾール、チオフェン、ジヒドロフェナントレン、インデノフルオレン、フェナントレン、芳香族ケトン、金属錯体、トリアリールアミン若しくは複数のこれら単位から選ばれる反復単位を有することを特徴とする請求項13項記載のポリマー、オリゴマー若しくはデンドリマー。
- 請求項1乃至14項の何れか1項記載の化合物の有機電子素子での使用。
- 請求項1乃至14項の何れか1項記載の少なくとも1つの化合物を含む有機電子素子。
- 有機エレクトロルミネッセンス素子(OLED)、有機電界効果トランジスタ(O-FET)、有機薄膜トランジスタ(O-TFT)、有機光放出トランジスタ(O-LET)、有機集積回路(O-IC)、有機太陽電池(O-SC)、有機電場消光素子(O-FQD)、光放出電子化学電池(LEC)、有機光受容器及び有機レーザーダイオード(O-laser)からなる群より選択されることを特徴とする請求項16記載の有機電子素子。
- 発光層が請求項1乃至14項の何れか1項記載の少なくとも1つの化合物を含むことを特徴とする、陽極、陰極及び少なくとも1つの発光層を含む有機エレクトロルミネッセンス素子。
- 請求項1乃至14項の何れか1項記載の化合物がエミッターとして使用され、発光層の母体材料が、オリゴアリーレン、縮合芳香族基を含むオリゴアリーレン、オリゴアリーレンビニレン、ポリポダル多価金属錯体、正孔伝導化合物、電子伝導化合物、ケトン、ホスフィン酸化物、スルホキシド及びアトロプ異性体のクラスから選ばれることを特徴とする請求項18記載の有機エレクトロルミネッセンス素子。
- 正孔注入層、正孔輸送層、正孔障壁層、電子輸送層及び/又は電子注入層から選ばれる更なる層が存在することを特徴とする請求項18若しくは19項記載の有機エレクトロルミネッセンス素子。
- 請求項1乃至14項の何れか1項記載の化合物が、正孔輸送層における及び/又は正孔注入層における正孔輸送材料として使用され、これらの層の化合物が電子受容化合物により随意にドープされていてもよいことを特徴とする請求項16乃至20項記載の有機電子素子。
- 請求項1乃至14項の何れか1項記載の化合物が、電子輸送層における電子輸送材料として及び/又は正孔障壁層における正孔障壁材料として及び/又は発光層におけるトリプレット母体材料として使用されることを特徴とする請求項16乃至21項の何れか1項記載の有機電子素子。
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KR101346467B1 (ko) | 2014-01-02 |
US20080220285A1 (en) | 2008-09-11 |
RU2419648C2 (ru) | 2011-05-27 |
TW200706636A (en) | 2007-02-16 |
MX2007014449A (es) | 2008-02-07 |
EP1883688B1 (de) | 2018-04-11 |
EP1883688A1 (de) | 2008-02-06 |
KR20080015865A (ko) | 2008-02-20 |
AU2006246743A1 (en) | 2006-11-23 |
US9461249B2 (en) | 2016-10-04 |
AU2006246743B2 (en) | 2012-05-31 |
CA2608765A1 (en) | 2006-11-23 |
RU2007146793A (ru) | 2009-06-27 |
DE102005023437A1 (de) | 2006-11-30 |
CN101228250A (zh) | 2008-07-23 |
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US8852756B2 (en) | 2014-10-07 |
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US20150031896A1 (en) | 2015-01-29 |
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