JP2017529689A - 電子緩衝材及び有機エレクトロルミネセントデバイス - Google Patents
電子緩衝材及び有機エレクトロルミネセントデバイス Download PDFInfo
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- JP2017529689A JP2017529689A JP2017504664A JP2017504664A JP2017529689A JP 2017529689 A JP2017529689 A JP 2017529689A JP 2017504664 A JP2017504664 A JP 2017504664A JP 2017504664 A JP2017504664 A JP 2017504664A JP 2017529689 A JP2017529689 A JP 2017529689A
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- substituted
- unsubstituted
- aryl
- compound
- alkyl
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- 239000000872 buffer Substances 0.000 title claims abstract description 79
- 239000000463 material Substances 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims description 80
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 32
- -1 cyano, carboxyl Chemical group 0.000 claims description 27
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 238000002347 injection Methods 0.000 claims description 21
- 239000007924 injection Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000005104 aryl silyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000001769 aryl amino group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 239000002019 doping agent Substances 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000003367 polycyclic group Chemical group 0.000 claims description 8
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000005054 naphthyridines Chemical class 0.000 claims description 2
- 150000005041 phenanthrolines Chemical class 0.000 claims description 2
- 150000003216 pyrazines Chemical class 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 150000003248 quinolines Chemical class 0.000 claims description 2
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 2
- 150000002910 rare earth metals Chemical class 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000005382 boronyl group Chemical group 0.000 claims 1
- 229910052733 gallium Inorganic materials 0.000 claims 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 claims 1
- 239000010410 layer Substances 0.000 description 124
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 238000003775 Density Functional Theory Methods 0.000 description 4
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 4
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 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 3
- 238000007740 vapor deposition Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 2
- GJWBRYKOJMOBHH-UHFFFAOYSA-N 9,9-dimethyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]-n-(4-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 GJWBRYKOJMOBHH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
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- 239000000243 solution Substances 0.000 description 2
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- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
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- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- DZINJFQFEBORIC-UHFFFAOYSA-N 12h-[1]benzofuro[2,3-a]carbazole Chemical compound C12=CC=CC=C2OC2=C1C=CC1=C2NC2=CC=CC=C12 DZINJFQFEBORIC-UHFFFAOYSA-N 0.000 description 1
- CILATXQQOGDBRQ-UHFFFAOYSA-N 12h-[1]benzothiolo[2,3-a]carbazole Chemical compound C12=CC=CC=C2SC2=C1C=CC1=C2NC2=CC=CC=C12 CILATXQQOGDBRQ-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
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- RZVPFDOTMFYQHR-UHFFFAOYSA-N 2-chloro-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(Cl)=N1 RZVPFDOTMFYQHR-UHFFFAOYSA-N 0.000 description 1
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 101000687716 Drosophila melanogaster SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 homolog Proteins 0.000 description 1
- 101000687741 Mus musculus SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 Proteins 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
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- 125000005605 benzo group Chemical group 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
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- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
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- 235000010290 biphenyl Nutrition 0.000 description 1
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- 238000004364 calculation method Methods 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002484 cyclic voltammetry 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
- 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 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
- 238000006731 degradation reaction Methods 0.000 description 1
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- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000002258 gallium Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000003854 isothiazoles Chemical class 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010189 synthetic method Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 150000004867 thiadiazoles Chemical class 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
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000002061 vacuum sublimation Methods 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
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Abstract
Description
Xは、OまたはSを表し;
Lは、単結合、置換若しくは非置換の(C6−C30)アリーレン、または置換若しくは非置換の5から30員環のヘテロアリーレンを表し;
Aは、置換または非置換の5から30員環のヘテロアリールを表し;
R1及びR2はそれぞれ独立して、水素、重水素、ハロゲン、シアノ、置換若しくは非置換の(C1−C30)アルキル、置換若しくは非置換の(C6−C30)アリール、置換若しくは非置換の5から30員環のヘテロアリール、置換若しくは非置換の(C6−C30)アリール(C1−C30)アルキル、置換若しくは非置換の(C3−C30)シクロアルキル、置換若しくは非置換の(C1−C30)アルコキシ、置換若しくは非置換の(C1−C30)アルキルシリル、置換若しくは非置換の(C6−C30)アリールシリル、置換若しくは非置換の(C6−C30)アリール(C1−C30)アルキルシリル、置換若しくは非置換の(C1−C30)アルキルアミノ、置換若しくは非置換の(C6−C30)アリールアミノ;または置換若しくは非置換の(C1−C30)アルキル(C6−C30)アリールアミノを表し;または隣接する一つまたは複数の置換基に結合して、その一つまたは複数の炭素原子が窒素、酸素及び硫黄から選択される少なくとも一つのヘテロ原子で置換されてもよい単環または多環(C3−C30)の脂環式または芳香族環を形成し、
R3は、水素、重水素、ハロゲン、シアノ、置換若しくは非置換の(C1−C30)アルキル、置換若しくは非置換の(C6−C30)アリール、または置換若しくは非置換の5から30員環のヘテロアリールを表し、または隣接する一つまたは複数の置換基に結合して、その一つまたは複数の炭素原子が窒素、酸素及び硫黄から選択される少なくとも一つのヘテロ原子で置換されてもよい単環または多環の(C3−C30)脂環式または芳香族環を形成し;
a及びbはそれぞれ独立して、1から4の整数を表し;ここで、またはbは、2以上の整数であり、R1の各々及びR2の各々は、同じでも異なってもよく;
cは、1から2の整数を表し、ここでcは2であり、R3の各々は、同じでも異なってもよく;そして
ヘテロアリール(エン)は、B、N、O、S、Si、及びPから選択される少なくとも一つのヘテロ原子を含む。
100:有機エレクトロルミネセントデバイス
101:基板
110:第1の電極
120:有機層
122:正孔注入層
123:正孔輸送層
125:発光層
126:電子緩衝層
127:電子輸送層
128:電子注入層
129:電子輸送ゾーン
130:第2の電極
Claims (13)
- 下記の式1によって表される化合物を含む電子緩衝材であって:
Xは、OまたはSを表し;
Lは、単結合、置換若しくは非置換の(C6−C30)アリーレン、または置換若しくは非置換の5から30員環のヘテロアリーレンを表し;
Aは、置換または非置換の5から30員環のヘテロアリールを表し;
R1及びR2はそれぞれ独立して、水素、重水素、ハロゲン、シアノ、置換若しくは非置換の(C1−C30)アルキル、置換若しくは非置換の(C6−C30)アリール、置換若しくは非置換の5から30員環のヘテロアリール、置換若しくは非置換の(C6−C30)アリール(C1−C30)アルキル、置換若しくは非置換の(C3−C30)シクロアルキル、置換若しくは非置換の(C1−C30)アルコキシ、置換若しくは非置換の(C1−C30)アルキルシリル、置換若しくは非置換の(C6−C30)アリールシリル、置換若しくは非置換の(C6−C30)アリール(C1−C30)アルキルシリル、置換若しくは非置換の(C1−C30)アルキルアミノ、置換若しくは非置換の(C6−C30)アリールアミノ;または置換若しくは非置換の(C1−C30)アルキル(C6−C30)アリールアミノを表し;または隣接する一つまたは複数の置換基に結合して、その一つまたは複数の炭素原子が窒素、酸素及び硫黄から選択される少なくとも一つのヘテロ原子で置換されてもよい単環または多環(C3−C30)の脂環式または芳香族環を形成し;
R3は、水素、重水素、ハロゲン、シアノ、置換若しくは非置換の(C1−C30)アルキル、置換若しくは非置換の(C6−C30)アリール、または置換若しくは非置換の5から30員環のヘテロアリールを表し、または隣接する一つまたは複数の置換基に結合して、その一つまたは複数の炭素原子が窒素、酸素及び硫黄から選択される少なくとも一つのヘテロ原子で置換されてもよい単環または多環の(C3−C30)脂環式または芳香族環を形成し;
a及びbはそれぞれ独立して、1から4の整数を表し;ここで、aまたはbは、2以上の整数である場合、R1の各々及びR2の各々は、同じでも異なってもよく;
cは、1から2の整数を表し;ここでcは2である場合、R3の各々は、同じでも異なってもよく;そして
ヘテロアリール(エン)は、B、N、O、S、Si、及びPから選択される少なくとも一つのヘテロ原子を含む、電子緩衝材。 - L、A、及びR1からR3中の置換アルキル、置換アルコキシ、置換シクロアルキル、置換アリール(エン)、置換ヘテロアリール(エン)、置換アルキルシリル、置換アリールシリル、置換アリールアルキルシリル、置換アリールアミノ、置換アルキルアミノ、置換アルキルアリールアミノ、並びに置換アリールアルキルの置換基はそれぞれ独立に、重水素、ハロゲン、シアノ、カルボキシル、ニトロ、ヒドロキシ、(C1−C30)アルキル、ハロ(C1−C30)アルキル、(C2−C30)アルケニル、(C2−C30)アルキニル、(C1−C30)アルコキシ、(C1−C30)アルキルチオ、(C3−C30)シクロアルキル、(C3−C30)シクロアルケニル、3から7員環のヘテロシクロアルキル、(C6−C30)アリールオキシ、(C6−C30)アリールチオ、非置換または(C6−C30)アリールで置換された3から30員環のヘテロアリール、(C6−C30)アリール、3から30員環のヘテロアリールで置換された(C6−C30)アリール、トリ(C1−C30)アルキルシリルで置換された(C6−C30)アリール、トリ(C6−C30)アリールシリルで置換された(C6−C30)アリール、トリ(C1−C30)アルキルシリル、トリ(C6−C30)アリールシリル、ジ(C1−C30)アルキル(C6−C30)アリールシリル、(C1−C30)アルキルジ(C6−C30)アリールシリル、アミノ、モノまたはジ(C1−C30)アルキルアミノ、モノまたはジ(C6−C30)アリールアミノ、(C1−C30)アルキル(C6−C30)アリールアミノ、(C1−C30)アルキルカルボニル、(C1−C30)アルコキシカルボニル、(C6−C30)アリールカルボニル、ジ(C6−C30)アリールボロニル、ジ(C1−C30)アルキルボロニル、(C1−C30)アルキル(C6−C30)アリールボロニル、(C6−C30)アリール(C1−C30)アルキル、及び(C1−C30)アルキル(C6−C30)アリールから成る群から選択される少なくとも一つである、請求項1の電子緩衝材。
- Xは、OまたはSを表し;
Lは、単結合、置換若しくは非置換の(C6−C20)アリーレン、または置換若しくは非置換の5から20員環のヘテロアリーレンを表し;
Aは、置換または非置換の5から25員環のヘテロアリールを表し;
R1及びR2はそれぞれ独立して、水素、置換若しくは非置換の(C6−C20)アリール、または置換若しくは非置換の5から20員環のヘテロアリールを表し;
R3は、水素を表し;
a及びbはそれぞれ独立して、1から2の整数を表し、そして
cは、1を表す、請求項1の電子緩衝材。 - Xは、OまたはSを表し;
Lは、単結合、非置換(C6−C20)アリーレン、または非置換の5から20員環のヘテロアリーレンを表し;
Aは、非置換の5から25員環のヘテロアリール、シアノで置換された5から25員環のヘテロアリール、(C6−C25)アリールで置換された5から25員環のヘテロアリール、5から20員環のヘテロアリールで置換された5から25員環のヘテロアリール、または(C1−C6)アルキル(C6−C20)アリールで置換された5から25員環のヘテロアリールを表し;
R1及びR2はそれぞれ独立して、水素、非置換若しくは(C1−C6)アルキルで置換された(C6−C20)アリール、または非置換若しくは(C6−C20)アリールで置換された5から20員環のヘテロアリールを表し;
R3は、水素を表し;
a及びbはそれぞれ独立して、1から2の整数を表し;そして
cは1を表す、請求項1の電子緩衝材。 - Aは、置換若しくは非置換のピリジン、置換若しくは非置換のピリミジン、置換若しくは非置換のトリアジン、置換若しくは非置換のピラジン、置換若しくは非置換のキノリン、置換若しくは非置換のキナゾリン、置換若しくは非置換のキノキサリン、置換若しくは非置換ベンズイミダゾール、置換または非置換ナフチリジン、または置換若しくは非置換フェナントロリンを表す、請求項1の電子緩衝材。
- 第1の電極;前記第1の電極に向き合う第2の電極;前記第1の電極と前記第2の電極の間の発光層;並びに前記発光層と前記第2の電極の間の電子輸送ゾーン及び電子緩衝層を含む有機エレクトロルミネセントデバイスであって;
ここで前記電子緩衝層は、下記の式1によって表される化合物を含み:
Xは、OまたはSを表し;
Lは、単結合、置換若しくは非置換の(C6−C30)アリーレン、または置換若しくは非置換の5から30員環のヘテロアリーレンを表し;
Aは、置換または非置換の5から30員環のヘテロアリールを表し;
R1及びR2はそれぞれ独立して、水素、重水素、ハロゲン、シアノ、置換若しくは非置換の(C1−C30)アルキル、置換若しくは非置換の(C6−C30)アリール、置換もしくは非置換の5から30員環のヘテロアリール、置換若しくは非置換の(C6−C30)アリール(C1−C30)アルキル、置換若しくは非置換の(C3−C30)シクロアルキル、置換若しくは非置換の(C1−C30)アルコキシ、置換若しくは非置換の(C1−C30)アルキルシリル、置換もしくは非置換の(C6−C30)アリールシリル、置換若しくは非置換の(C6−C30)アリール(C1−C30)アルキルシリル、置換もしくは非置換の(C1−C30)アルキルアミノ、置換若しくは非置換の(C6−C30)アリールアミノ、または置換若しくは非置換の(C1−C30)アルキル(C6−C30)アリールアミノを表し;または隣接する一つまたは複数の置換基に結合して、その一つまたは複数の炭素原子が窒素、酸素及び硫黄から選択される少なくとも一つのヘテロ原子で置換されてもよい単環または多環の(C3−C30)脂環式または芳香族環を形成し;
R3は、水素、重水素、ハロゲン、シアノ、置換若しくは非置換の(C1−C30)アルキル、置換若しくは非置換の(C6−C30)アリール、または置換若しくは非置換の5から30員環ヘテロアリールを表し、または隣接する一つまたは複数の置換基に結合して、その一つまたは複数の炭素原子が窒素、酸素及び硫黄から選択される少なくとも一つのヘテロ原子で置換されてもよい単環または多環の(C3−C30)脂環式または芳香族環を形成し;
a及びbはそれぞれ独立して、1から4の整数を表し;ここでaまたはbは、2以上の整数である場合、R1及びR2の各々は、同じでも異なってもよく;
cは1から2の整数を表し;ここでcは2である場合、R3の各々は、同じでも異なってもよく;そして
ヘテロアリール(エン)は、B、N、O、S、Si及びPから選択される少なくとも一つのヘテロ原子を含む、有機エレクトロルミネセントデバイス。 - 前記発光層は、ホスト化合物及びドーパント化合物を含み、そして電子緩衝層のLUMO(最低空分子軌道)エネルギーレベルは、前記ホスト化合物のLUMOエネルギーレベルよりも大きい、請求項8の有機エレクトロルミネセントデバイス。
- 前記電子輸送ゾーンは、電子輸送化合物、還元性ドーパント、またはその組み合わせを含む、請求項8の有機エレクトロルミネセントデバイス。
- 前記電子輸送化合物は、オキサゾール系化合物、イソオキサゾール系化合物、トリアゾール系化合物、イソチアゾール系化合物、オキサジアゾール系化合物、チアジアゾール系化合物、ペリレン系化合物、アントラセン系化合物、アルミニウム錯体、及びガリウム錯体から成る群から選択される少なくとも1種であり;前記還元性ドーパントは、アルカリ金属、アルカリ金属化合物、アルカリ土類金属、希土類金属、そのハロゲン化物、その酸化物及びその錯体から成る群から選択される少なくとも1種である、請求項10の有機エレクトロルミネセントデバイス。
- 前記電子輸送ゾーンは、電子注入層、電子輸送層、またはその両方を含む、請求項8の有機エレクトロルミネセントデバイス。
- 第1の電極と発光層との間に、正孔注入層、正孔輸送層、またはその両方をさらに含む、請求項8の有機エレクトロルミネセントデバイス。
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CN106536527B (zh) | 2019-11-08 |
EP3174887A4 (en) | 2018-04-04 |
KR20160014556A (ko) | 2016-02-11 |
EP3174887A1 (en) | 2017-06-07 |
WO2016018076A1 (en) | 2016-02-04 |
US20170222159A1 (en) | 2017-08-03 |
CN106536527A (zh) | 2017-03-22 |
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