JP6547840B2 - スピロ型化合物及びこれを含む有機発光素子{spiro compound and organic light−emitting element comprising same} - Google Patents
スピロ型化合物及びこれを含む有機発光素子{spiro compound and organic light−emitting element comprising same} Download PDFInfo
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- JP6547840B2 JP6547840B2 JP2017551119A JP2017551119A JP6547840B2 JP 6547840 B2 JP6547840 B2 JP 6547840B2 JP 2017551119 A JP2017551119 A JP 2017551119A JP 2017551119 A JP2017551119 A JP 2017551119A JP 6547840 B2 JP6547840 B2 JP 6547840B2
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- 150000003413 spiro compounds Chemical class 0.000 title description 4
- -1 aryl phosphine Chemical compound 0.000 claims description 193
- 150000001875 compounds Chemical class 0.000 claims description 193
- 239000010410 layer Substances 0.000 claims description 149
- 239000000126 substance Substances 0.000 claims description 109
- 125000003118 aryl group Chemical group 0.000 claims description 83
- 238000002347 injection Methods 0.000 claims description 43
- 239000007924 injection Substances 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 239000012044 organic layer Substances 0.000 claims description 39
- 125000001769 aryl amino group Chemical group 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 230000005525 hole transport Effects 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002560 nitrile group Chemical group 0.000 claims description 14
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 10
- 230000001629 suppression Effects 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 9
- 239000011368 organic material Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims description 6
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 125000005165 aryl thioxy group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 6
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000005462 imide group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000005581 pyrene group Chemical group 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004653 anthracenylene group Chemical group 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 72
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 56
- 239000008096 xylene Substances 0.000 description 56
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 230000032258 transport Effects 0.000 description 34
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 33
- 239000000463 material Substances 0.000 description 32
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 29
- 229940125904 compound 1 Drugs 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 23
- 229940126062 Compound A Drugs 0.000 description 21
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 21
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 20
- 239000000758 substrate Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 125000003367 polycyclic group Chemical group 0.000 description 12
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 11
- 239000012153 distilled water Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 0 C*C(*=C(*1)c2cccc3c2[o]c2ccccc32)=*C1c1ccccc1 Chemical compound C*C(*=C(*1)c2cccc3c2[o]c2ccccc32)=*C1c1ccccc1 0.000 description 9
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000010405 anode material Substances 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 150000002391 heterocyclic compounds Chemical class 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- FJEKJOSACGHSMC-UHFFFAOYSA-N c1ccc2[nH]c(cc3Oc4ccccc4C4(c(cccc5)c5-[n]5c6c4cccc6c4ccccc54)c3c3)c3c2c1 Chemical compound c1ccc2[nH]c(cc3Oc4ccccc4C4(c(cccc5)c5-[n]5c6c4cccc6c4ccccc54)c3c3)c3c2c1 FJEKJOSACGHSMC-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 150000003852 triazoles Chemical group 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- DXRLALXPCIOIDK-UHFFFAOYSA-N 2-(4-bromophenyl)-1-phenylbenzimidazole Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 DXRLALXPCIOIDK-UHFFFAOYSA-N 0.000 description 2
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 2
- ZGNCKIDXVHSMJL-UHFFFAOYSA-N 2-methylquinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC=C21 ZGNCKIDXVHSMJL-UHFFFAOYSA-N 0.000 description 2
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
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- ICVVHQIMGGLJDN-UHFFFAOYSA-N C(Cc(cc1)ccc1-[n](c1ccccc11)c2c1c(Oc1c(C3(c4ccc5)c(cccc6)c6-[n]6c4c5c4ccccc64)cccc1)c3cc2)C1c2ccccc2-c2c1cccc2 Chemical compound C(Cc(cc1)ccc1-[n](c1ccccc11)c2c1c(Oc1c(C3(c4ccc5)c(cccc6)c6-[n]6c4c5c4ccccc64)cccc1)c3cc2)C1c2ccccc2-c2c1cccc2 ICVVHQIMGGLJDN-UHFFFAOYSA-N 0.000 description 1
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- WSKQNDLXMCCBNJ-UHFFFAOYSA-N C1C(c2ccccc2)=CC(c2ccccc2)=CC1[n]1c(cc(C(c2ccc3)(c(cccc4)c4-[n]4c2c3c2ccccc42)c(cccc2)c2S2)c2c2)c2c2c1cccc2 Chemical compound C1C(c2ccccc2)=CC(c2ccccc2)=CC1[n]1c(cc(C(c2ccc3)(c(cccc4)c4-[n]4c2c3c2ccccc42)c(cccc2)c2S2)c2c2)c2c2c1cccc2 WSKQNDLXMCCBNJ-UHFFFAOYSA-N 0.000 description 1
- SWYVBMVNOYHFIS-UHFFFAOYSA-N C1C(c2ccccc2)NC(c2ccccc2)=NC(c(cc2)ccc2-[n]2c(cc(C(c3ccc4)(c5ccccc5-[n]5c3c4c3ccccc53)c(cccc3)c3O3)c3c3)c3c3ccccc23)=CC1 Chemical compound C1C(c2ccccc2)NC(c2ccccc2)=NC(c(cc2)ccc2-[n]2c(cc(C(c3ccc4)(c5ccccc5-[n]5c3c4c3ccccc53)c(cccc3)c3O3)c3c3)c3c3ccccc23)=CC1 SWYVBMVNOYHFIS-UHFFFAOYSA-N 0.000 description 1
- GQRAOIZJLCDKHE-UHFFFAOYSA-N C1C=CC(c2nc(-[n]3c4cc(Sc5ccccc5C56c(cccc7)c7-[n]7c8c5cccc8c5c7cccc5)c6cc4c4c3cccc4)nc(-c3ccccc3)n2)=CC1 Chemical compound C1C=CC(c2nc(-[n]3c4cc(Sc5ccccc5C56c(cccc7)c7-[n]7c8c5cccc8c5c7cccc5)c6cc4c4c3cccc4)nc(-c3ccccc3)n2)=CC1 GQRAOIZJLCDKHE-UHFFFAOYSA-N 0.000 description 1
- UBEHUISPCHOQJZ-UHFFFAOYSA-N C1C=CC(c2nc(C3=CC=CCC3)cc(-c3cccc(-[n](c4ccccc44)c5c4c(Sc4c(C6(c7ccc8)c9ccccc9-[n]9c7c8c7ccccc97)cccc4)c6cc5)c3)n2)=CC1 Chemical compound C1C=CC(c2nc(C3=CC=CCC3)cc(-c3cccc(-[n](c4ccccc44)c5c4c(Sc4c(C6(c7ccc8)c9ccccc9-[n]9c7c8c7ccccc97)cccc4)c6cc5)c3)n2)=CC1 UBEHUISPCHOQJZ-UHFFFAOYSA-N 0.000 description 1
- CXFZBHFDUYKEPW-UHFFFAOYSA-N C1C=CC=CC1c1nc(-c2cc(-[n]3c(cc(C4(c(cccc5)c5-[n]5c6c4cccc6c4ccccc54)c(cccc4)c4S4)c4c4)c4c4c3cccc4)ccc2)cc(-c2ccccc2)n1 Chemical compound C1C=CC=CC1c1nc(-c2cc(-[n]3c(cc(C4(c(cccc5)c5-[n]5c6c4cccc6c4ccccc54)c(cccc4)c4S4)c4c4)c4c4c3cccc4)ccc2)cc(-c2ccccc2)n1 CXFZBHFDUYKEPW-UHFFFAOYSA-N 0.000 description 1
- CSNQNWVDSFABRP-UHFFFAOYSA-N CC(C1)C=CC(C2(c(cccc3)c3Oc3c4)c3cc3c4c4ccccc4[n]3C(C3)C=CC=C3c3cc(-c4ccccc4)nc(-c4ccccc4)n3)=C1[n]1c3c2cccc3c2ccccc12 Chemical compound CC(C1)C=CC(C2(c(cccc3)c3Oc3c4)c3cc3c4c4ccccc4[n]3C(C3)C=CC=C3c3cc(-c4ccccc4)nc(-c4ccccc4)n3)=C1[n]1c3c2cccc3c2ccccc12 CSNQNWVDSFABRP-UHFFFAOYSA-N 0.000 description 1
- MMYPSPYDMXFXQF-UHFFFAOYSA-N CC(C1)C=CC(C2(c3ccc4)c(cccc5)c5SC5=C2CC=C(c(cccc2)c2N2c6cccc(-c7nc(-c8ccccc8)nc(-c8ccccc8)c7)c6)C2=C5)=C1[n]1c3c4c2ccccc12 Chemical compound CC(C1)C=CC(C2(c3ccc4)c(cccc5)c5SC5=C2CC=C(c(cccc2)c2N2c6cccc(-c7nc(-c8ccccc8)nc(-c8ccccc8)c7)c6)C2=C5)=C1[n]1c3c4c2ccccc12 MMYPSPYDMXFXQF-UHFFFAOYSA-N 0.000 description 1
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- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer Methods 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
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- NVCBVYYESHBQKS-UHFFFAOYSA-L zinc;2-carboxyquinolin-8-olate Chemical compound [Zn+2].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 NVCBVYYESHBQKS-UHFFFAOYSA-L 0.000 description 1
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- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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Description
(化学式1)
YはO、SまたはSiR11R12であり、
XはNAr、OまたはSであり、
R1〜R8及びArは互いに同一であるかまたは異なり、各々独立して水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミノ基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアラルキル基;置換もしくは非置換のアラルケニル基;置換もしくは非置換のアルキルアリール基;置換もしくは非置換のアルキルアミノ基;置換もしくは非置換のアラルキルアミノ基;置換もしくは非置換のヘテロアリールアミノ基;置換もしくは非置換のアリールアミノ基;置換もしくは非置換のアリールヘテロアリールアミノ基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換の複素環基であるか、隣接した基と互いに結合して環を形成することができ、R11及びR12は互いに同一であるかまたは異なり、各々独立して水素;重水素;置換もしくは非置換のアルキル基;または置換もしくは非置換のアリール基であり、p、s、r及びuは各々0〜4の整数であり、qは0〜3の整数であり、tは0〜2の整数であり、p、q、r、s、t及びuが各々2以上である場合、括弧内の基は互いに同一であるかまたは異なる。
(化学式3)
(化学式4)
(化学式8)
本発明の一実施態様によれば、Ar1は下記構造式の中から選択される。
(化学式1−A)
n1は1以上の整数であり、
Ar7は置換もしくは非置換の1価以上のベンゾフルオレン基;置換もしくは非置換の1価以上のフルオランテン基;置換もしくは非置換の1価以上のピレン基;または置換もしくは非置換の1価以上のクリセン基であり、
L4は直接結合;置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
Ar8及びAr9は互いに同一であるかまたは異なり、各々独立して置換もしくは非置換のアリール基;置換もしくは非置換のシリル基;置換もしくは非置換のゲルマニウム基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリールアルキル基;または置換もしくは非置換のヘテロアリール基であるか、互いに結合して置換もしくは非置換の環を形成することができ、
n1が2以上である場合、2以上の括弧内の構造は互いに同一であるかまたは異なる。
G11は1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基または下記化学式
G12はフェニル基、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、9−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、2−ビフェニリル基、3−ビフェニリル基、4−ビフェニリル基、p−テルフェニル−4−イル基、p−テルフェニル−3−イル基、p−テルフェニル−2−イル基、m−テルフェニル−4−イル基、m−テルフェニル−3−イル基、m−テルフェニル−2−イル基、o−トリル基、m−トリル基、p−トリル基、p−t−ブチルフェニル基、p−(2−フェニルプロピル)フェニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基、4−メチル−1−アントリル基、4'−メチルビフェニリル基、4''−t−ブチル−p−テルフェニル−4−イル基または3−フルオランテニル基であり、
G13及びG14は互いに同一であるかまたは異なり、各々独立して水素;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
g12は1〜5の整数であり、
g13及びg14は各々1〜4の整数であり、
前記g12〜g14が各々2以上である場合、2以上の括弧内の構造は互いに同一であるかまたは異なる。
MS[M+H]+=752
MS[M+H]+=754
MS[M+H]+=871
MS[M+H]+=742
MS[M+H]+=741
MS[M+H]+=741
MS[M+H]+=740
MS[M+H]+=715
MS[M+H]+=818
MS[M+H]+=818
MS[M+H]+=787
MS[M+H]+=677
MS[M+H]+=693
ITO(indium tin oxide)が1,000Å厚さで薄膜コーティングされたガラス基板を洗剤を溶かした蒸留水に入れて超音波で洗浄した。この時、洗剤としてはFischer社製のものを用い、蒸留水としてはMillipore社製のフィルタ(Filter)で2次濾過された蒸留水を用いた。ITOを30分間洗浄した後、蒸留水で2回繰り返して超音波洗浄を10分間行った。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノールの溶剤で超音波洗浄をして乾燥させた後にプラズマ洗浄機に輸送した。また、酸素プラズマを用いて前記基板を5分間洗浄した後に真空蒸着機に基板を輸送した。
このように準備したITO透明電極上に下記化学式のヘキサニトリルヘキサアザトリフェニレン(HAT)を500Å厚さで熱真空蒸着して正孔注入層を形成した。
前記実験例1−1において化合物1の代わりに前記化合物2を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物3を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物15を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物16を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物17を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物29を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物30を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物31を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物43を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物58を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物73を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物85を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物100を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物115を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物127を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物142を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物157を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物169を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物184を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物199を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりに前記化合物211を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
前記実験例1−1において化合物1の代わりにEB2を用いたことを除いては、実験例1−1と同様の方法により有機発光素子を製作した。
本発明に係る化学式の化合物誘導体は電子抑制能力に優れて低電圧及び高効率の特性を示しており、有機発光素子に適用可能であることを確認することができた。
合成例で合成された化合物を通常に知られた方法で高純度の昇華精製をした後、下記のような方法により緑色有機発光素子を製造した。
ITO(indium tin oxide)が1,000Å厚さで薄膜コーティングされたガラス基板を洗剤を溶かした蒸留水に入れて超音波で洗浄した。この時、洗剤としてはFischer社製のものを用い、蒸留水としてはMillipore社製のフィルタ(Filter)で2次濾過された蒸留水を用いた。ITOを30分間洗浄した後、蒸留水で2回繰り返して超音波洗浄を10分間行った。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノールの溶剤で超音波洗浄をして乾燥させた後にプラズマ洗浄機に輸送した。また、酸素プラズマを用いて前記基板を5分間洗浄した後に真空蒸着機に基板を輸送した。
このように準備したITO透明電極上に、化合物4をホストとして用いて、m−MTDATA(60nm)/TCTA(80nm)/化合物4+10%Ir(ppy)3(300nm)/BCP(10nm)/Alq3(30nm)/LiF(1nm)/Al(200nm)順に発光素子を構成して有機発光素子を製造した。
m−MTDATA、TCTA、Ir(ppy)3及びBCPの各々の構造は次のとおりである。
前記実験例2−1において化合物4の代わりに前記化合物5を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりに前記化合物6を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりに前記化合物7を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりに前記化合物9を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりに前記化合物10を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりに前記化合物18を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりに前記化合物19を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりに前記化合物20を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりに前記化合物21を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりに前記化合物23を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりに前記化合物24を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりに前記化合物32を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
前記実験例2−1において化合物4の代わりにGH2を用いたことを除いては、実験例2−1と同様の方法により有機発光素子を製作した。
合成例で合成された化合物を通常に知られた方法で高純度の昇華精製をした後、下記のような方法により赤色有機発光素子を製造した。
ITOガラスの発光面積が2mm×2mm大きさになるようにパターニングした後に洗浄した。基板を真空チャンバに取り付けた後、ベース圧力が1×10−6torrになるようにした後、前記ITO上にDNTPD(700Å)及びα−NPB(300Å)を用いて層を順次形成した。次に、化合物8をホストとして(90wt%)用い、ドーパントとして下記(piq)2Ir(acac)(10wt%)を共蒸着(300Å)して発光層を形成し、さらにAlq3(350Å)、LiF(5Å)、Al(1,000Å)の順に成膜した後、0.4mAで測定をした。
前記DNTPD、α−NPB、(piq)2Ir(acac)及びAlq3の構造は次のとおりである。
前記実験例3−1において化合物8の代わりに前記化合物22を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物36を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物50を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物64を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物78を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物92を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物106を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物120を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物134を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物148を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物162を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物176を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物190を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
前記実験例3−1において化合物8の代わりに前記化合物204を用いたことを除いては、実験例3−1と同様の方法により有機発光素子を製作した。
比較例3−1のための有機発光素子は、前記実施例の素子構造において、発光層のホストとして、本発明により製造された有機発光化合物の代わりに、一般の燐光ホスト物質として多く用いられている下記化合物CBPを用いたことを除いては同様に製作した。
2 ・・・陽極
3 ・・・発光層
4 ・・・陰極
5 ・・・正孔注入層
6 ・・・正孔輸送層
7 ・・・電子輸送層
Claims (20)
- 下記化学式1で表される化合物:
(化学式1)
YはO、SまたはSiR11R12であり、
XはNArであり、
R1〜R8及びArは互いに同一であるかまたは異なり、各々独立して水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミノ基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアラルキル基;置換もしくは非置換のアラルケニル基;置換もしくは非置換のアルキルアリール基;置換もしくは非置換のアルキルアミノ基;置換もしくは非置換のアラルキルアミノ基;置換もしくは非置換のヘテロアリールアミノ基;置換もしくは非置換のアリールアミノ基;置換もしくは非置換のアリールヘテロアリールアミノ基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換の複素環基であるか、隣接した基と互いに結合して環を形成することができ、R11及びR12は互いに同一であるかまたは異なり、各々独立して水素;置換もしくは非置換のアルキル基;または置換もしくは非置換のアリール基であり、p、s、r及びuは各々0〜4の整数であり、qは0〜3の整数であり、tは0〜2の整数であり、p、q、r、s、t及びuが各々2以上である場合、括弧内の基は互いに同一であるかまたは異なる。 - XはNArであり、Arは−(L1)n−Ar1で表され、
L1は直接結合;置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレンであり、nは0〜2の整数であり、nが2の場合、L1は互いに同一であるかまたは異なり、
Ar1は水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミノ基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアラルキル基;置換もしくは非置換のアラルケニル基;置換もしくは非置換のアルキルアリール基;置換もしくは非置換のアルキルアミノ基;置換もしくは非置換のアラルキルアミノ基;置換もしくは非置換のヘテロアリールアミノ基;置換もしくは非置換のアリールアミノ基;置換もしくは非置換のアリールヘテロアリールアミノ基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換の複素環基である、請求項1に記載の化合物。 - Ar1は置換もしくは非置換のアリール基;置換もしくは非置換の複素環基;置換もしくは非置換のアリールアミノ基;または置換もしくは非置換のアリールホスフィンである、請求項5に記載の化合物。
- L1は直接結合または置換もしくは非置換のアリーレンである、請求項5に記載の化合物。
- L1は直接結合、フェニレン、ビフェニリレン、ターフェニリレン、クォーターフェニリレン、ナフチレン、アントリレン、フルオレン、フェナントレン、ピレンまたはトリフェニレンである、請求項5に記載の化合物。
- 第1電極、前記第1電極と対向して備えられた第2電極、及び前記第1電極と前記第2電極との間に備えられた1層以上の有機物層を含む有機発光素子であって、前記有機物層のうち1層以上は請求項1〜9のいずれか1項に記載の化合物を含む有機発光素子。
- 前記有機物層は正孔輸送層を含み、前記正孔輸送層は前記化合物を含む、請求項10に記載の有機発光素子。
- 前記有機物層は正孔注入層を含み、前記正孔注入層は前記化合物を含む、請求項10に記載の有機発光素子。
- 前記有機物層は発光層を含み、前記発光層は前記化合物を含む、請求項10に記載の有機発光素子。
- 前記有機物層は電子抑制層を含み、前記電子抑制層は前記化合物を含む、請求項10に記載の有機発光素子。
- 前記有機物層は正孔注入と正孔輸送を同時にする層を含み、前記正孔注入と正孔輸送を同時にする層は前記化合物を含む、請求項10に記載の有機発光素子。
- 前記有機物層は下記化学式1−Aで表される化合物を含む、請求項10に記載の有機発光素子:
(化学式1−A)
n1は1以上の整数であり、
Ar7は置換もしくは非置換の1価以上のベンゾフルオレン基;置換もしくは非置換の1価以上のフルオランテン基;置換もしくは非置換の1価以上のピレン基;または置換もしくは非置換の1価以上のクリセン基であり、
L4は直接結合;置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
Ar8及びAr9は互いに同一であるかまたは異なり、各々独立して置換もしくは非置換のアリール基;置換もしくは非置換のシリル基;置換もしくは非置換のゲルマニウム基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリールアルキル基;または置換もしくは非置換のヘテロアリール基であるか、互いに結合して置換もしくは非置換の環を形成することができ、
n1が2以上である場合、2以上の括弧内の構造は互いに同一であるかまたは異なる。 - 前記L4は直接結合であり、Ar7は2価のピレン基であり、Ar8及びAr9は互いに同一であるかまたは異なり、各々独立して炭素数1〜30のアルキル基で置換もしくは非置換された炭素数6〜30のアリール基、または置換もしくは非置換の炭素数2〜30のヘテロアリール基であり、n1は2である、請求項16に記載の有機発光素子。
- 前記有機物層は下記化学式2−Aで表される化合物を含む、請求項10に記載の有機発光素子:
(化学式2−A)
G11はフェニル基、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基または下記化学式
G12はフェニル基、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、9−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、2−ビフェニリル基、3−ビフェニリル基、4−ビフェニリル基、p−テルフェニル−4−イル基、p−テルフェニル−3−イル基、p−テルフェニル−2−イル基、m−テルフェニル−4−イル基、m−テルフェニル−3−イル基、m−テルフェニル−2−イル基、o−トリル基、m−トリル基、p−トリル基、p−t−ブチルフェニル基、p−(2−フェニルプロピル)フェニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基、4−メチル−1−アントリル基、4'−メチルビフェニリル基、4''−t−ブチル−p−テルフェニル−4−イル基または3−フルオランテニル基であり、
G13及びG14は互いに同一であるかまたは異なり、各々独立して水素;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
g12は1〜5の整数であり、
g13及びg14は各々1〜4の整数であり、
前記g12〜g14が各々2以上である場合、2以上の括弧内の構造は互いに同一であるかまたは異なる。 - 前記G11は1−ナフチル基であり、G12は2−ナフチル基である、請求項18に記載の有機発光素子。
- 前記有機物層は下記化学式2−Aで表される化合物を含む、請求項16に記載の有機発光素子:
(化学式2−A)
G11はフェニル基、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基または下記化学式
G12はフェニル基、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、9−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、2−ビフェニリル基、3−ビフェニリル基、4−ビフェニリル基、p−テルフェニル−4−イル基、p−テルフェニル−3−イル基、p−テルフェニル−2−イル基、m−テルフェニル−4−イル基、m−テルフェニル−3−イル基、m−テルフェニル−2−イル基、o−トリル基、m−トリル基、p−トリル基、p−t−ブチルフェニル基、p−(2−フェニルプロピル)フェニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基、4−メチル−1−アントリル基、4'−メチルビフェニリル基、4''−t−ブチル−p−テルフェニル−4−イル基または3−フルオランテニル基であり、
G13及びG14は互いに同一であるかまたは異なり、各々独立して水素;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
g12は1〜5の整数であり、
g13及びg14は各々1〜4の整数であり、
前記g12〜g14が各々2以上である場合、2以上の括弧内の構造は互いに同一であるかまたは異なる。
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