JP2020513685A - 有機エレクトロルミネセント材料及びそれを含む有機エレクトロルミネセントデバイス - Google Patents
有機エレクトロルミネセント材料及びそれを含む有機エレクトロルミネセントデバイス Download PDFInfo
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- JP2020513685A JP2020513685A JP2019525002A JP2019525002A JP2020513685A JP 2020513685 A JP2020513685 A JP 2020513685A JP 2019525002 A JP2019525002 A JP 2019525002A JP 2019525002 A JP2019525002 A JP 2019525002A JP 2020513685 A JP2020513685 A JP 2020513685A
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- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- organic electroluminescent
- alkyl
- ring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000463 material Substances 0.000 title claims abstract description 78
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 239000002019 doping agent Substances 0.000 claims description 36
- -1 cyano, carboxyl Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 11
- 125000005549 heteroarylene group Chemical group 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- 125000005104 aryl silyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino 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
- 125000000304 alkynyl 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
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 238000010586 diagram Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 99
- 238000002347 injection Methods 0.000 description 21
- 239000007924 injection Substances 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 20
- 230000000903 blocking effect Effects 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 11
- 239000003086 colorant Substances 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 7
- 150000001555 benzenes Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- AMSJIGYDHCSSRE-UHFFFAOYSA-N 3,14-diazahexacyclo[11.11.0.02,10.04,9.015,24.016,21]tetracosa-1(24),2,4,6,8,10,12,14,16,18,20,22-dodecaene Chemical class C1=CC=C2C=CC3=C4C5=NC6=CC=CC=C6C5=CC=C4N=C3C2=C1 AMSJIGYDHCSSRE-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 150000004770 chalcogenides Chemical class 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 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 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- UUESRJFGZMCELZ-UHFFFAOYSA-K aluminum;2-methylquinoline-8-carboxylate;4-phenylphenolate Chemical compound [Al+3].C1=CC([O-])=CC=C1C1=CC=CC=C1.C1=CC=C(C([O-])=O)C2=NC(C)=CC=C21.C1=CC=C(C([O-])=O)C2=NC(C)=CC=C21 UUESRJFGZMCELZ-UHFFFAOYSA-K 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000011248 coating agent Substances 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
- 230000007423 decrease Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000000469 dry deposition Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 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
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005286 illumination Methods 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
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 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
- 230000000737 periodic effect Effects 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
- 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
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 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
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 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
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005551 pyridylene 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
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000010189 synthetic method Methods 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
- 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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Abstract
Description
R1及びR2は、それぞれ独立して、水素、重水素、置換若しくは非置換の(C1−C10)アルキル、置換若しくは非置換の(C2−C10)アルケニル又は置換若しくは非置換の(C6−C30)アリールを表し、但し、R1及びR2の両方が水素であることはなく、
R3〜R5は、それぞれ独立して、水素、重水素、置換若しくは非置換の(C1−C10)アルキル又は置換若しくは非置換の(C6−C30)アリールを表し、及び
aは、1〜6の整数を表し、且つbは、1〜4の整数を表し、ここで、a及びbがそれぞれ独立して2以上の整数である場合、R1及びR2のそれぞれは、同一であるか又は異なり得る。)
A環及びB環は、それぞれ独立して、置換若しくは非置換のベンゼン環又は置換若しくは非置換のナフタレン環を表し、但し、A環及びB環の少なくとも1つは、置換又は非置換のナフタレン環であり、
Ar1及びAr2は、それぞれ独立して、置換若しくは非置換の(C6−C30)アリール又は置換若しくは非置換の窒素含有(8〜30員)ヘテロアリールを表し、
L1及びL2は、それぞれ独立して、単結合、置換若しくは非置換の(C6−C30)アリーレン又は置換若しくは非置換の(3〜30員)ヘテロアリーレンを表し、及び
ヘテロアリール(ヘテロアリーレン)は、B、N、O、S、Si及びPから選択される少なくとも1つのヘテロ原子を含有する。)
本開示により、優れた色純度を有する有機エレクトロルミネセントデバイスが提供され得る。
本開示による有機エレクトロルミネセント化合物を用いてOLEDデバイスを作製した。OLEDデバイス(ジオマテック株式会社、日本)のためのガラス基板上の透明電極酸化インジウムスズ(ITO)薄膜(10Ω/sq)をアセトン、エタノール及び蒸留水で超音波洗浄し、その後、イソプロパノール中に保存した。次いで、ITO基板を真空蒸着装置の基板ホルダーに取り付けた。化合物HI−1を真空蒸着装置のセルに導入した後、装置のチャンバー内の圧力を10−6トールに制御した。その後、セルに電流を流して、上記で導入した材料を蒸発させて、それによりITO基板上に厚さ80nmの第1の正孔注入層を形成した。次に、化合物HI−2を真空蒸着装置の別のセルに導入し、セルに電流を流して蒸着させ、それにより第1の正孔注入層上に厚さ5nmの第2の正孔注入層を形成した。次いで、化合物HT−1を真空蒸着装置の別のセルに導入し、セルに電流を流して蒸着させ、それにより第2の正孔注入層上に厚さ10nmの第1の正孔輸送層を形成した。次いで、化合物HT−2を真空蒸着装置の別のセルに導入し、セルに電流を流して蒸発させ、それにより第1の正孔輸送層上に厚さ60nmの第2の正孔輸送層を形成した。正孔注入層及び正孔輸送層を形成した後、以下のようにしてそれらの上に発光層を形成した。化合物H−2をホストとして真空蒸着装置の一方のセルに導入し、化合物D−19をドーパントとして他方のセルに導入した。ドーパントは、ホストとドーパントとの総量に基づいて3重量%のドーピング量で蒸着し、第2の正孔輸送層上に40nmの厚さの発光層を形成した。次いで、化合物ET−1と化合物EI−1とを他の2つのセルに導入し、1:1の割合で蒸着し、発光層上に厚さ35nmの電子輸送層を形成した。電子輸送層上に厚さ2nmの電子注入層として化合物EI−1を蒸着した後、電子注入層上に別の真空蒸着装置によって厚さ80nmのAlカソードを蒸着した。このようにしてOLEDデバイスを作製した。
化合物HT−2の代わりに第2の正孔輸送層として化合物HT−3を使用し、ドーパントとして化合物D−7を使用したことを除いて、デバイスの実施例1と同じ方法でOLEDデバイスを作製した。
化合物HI−1を厚さ90nmの第1の正孔注入層として堆積させ、化合物HT−2の代わりに第2の正孔輸送層として化合物HT−3を用い、ドーパントとして化合物D−9を用い、ドーパントをホストとドーパントとの総量に基づいて2重量%のドーピング量で蒸着したことを除いて、デバイスの実施例1と同じ方法でOLEDデバイスを作製した。
ドーパントとして下記化合物Aを使用したことを除いて、デバイスの実施例1と同じ方法でOLEDデバイスを作製した。
ドーパントとして下記化合物Bを使用したことを除いて、デバイスの実施例1と同じ方法でOLEDデバイスを作製した。
ドーパントとして上記化合物Bを使用し、化合物HT−2の代わりに化合物HT−3を第2の正孔輸送層として使用したことを除いて、デバイスの実施例1と同じ方法でOLEDデバイスを作製した。
色再現範囲は、National Television System Committee(NTSC)によって作成された色空間の規格に基づいて算出され、これは、国際照明委員会(CIE)によって定義された色座標系に基づいている。図1を参照して、NTSCによって定義される赤色(0.67、0.33)、緑色(0.21、0.71)及び青色(0.14、0.08)の3点で形成される三角形の面積が算出される(以下、「NTSC面積」)。また、青色及び緑色についてNTSC定義値を、赤色について、作製したデバイスでの測定値を用いて三角形の面積を算出し、次いでNTSC面積に対する三角形の面積の比を算出する。数字が高いほど、より鮮やかな色が再現される。
Claims (8)
- 下記の式1:
R1及びR2は、それぞれ独立して、水素、重水素、置換若しくは非置換の(C1−C10)アルキル、置換若しくは非置換の(C2−C10)アルケニル又は置換若しくは非置換の(C6−C30)アリールを表し、但し、R1及びR2の両方が水素であることはなく、
R3〜R5は、それぞれ独立して、水素、重水素、置換若しくは非置換の(C1−C10)アルキル又は置換若しくは非置換の(C6−C30)アリールを表し、及び
aは、1〜6の整数を表し、且つbは、1〜4の整数を表し、ここで、a及びbがそれぞれ独立して2以上の整数である場合、R1及びR2のそれぞれは、同一であるか又は異なり得る)
によって表される少なくとも1つの化合物と、
下記の式2:
A環及びB環は、それぞれ独立して、置換若しくは非置換のベンゼン環又は置換若しくは非置換のナフタレン環を表し、但し、A環及びB環の少なくとも1つは、置換又は非置換のナフタレン環であり、
Ar1及びAr2は、それぞれ独立して、置換若しくは非置換の(C6−C30)アリール又は置換若しくは非置換の窒素含有(8〜30員)ヘテロアリールを表し、
L1及びL2は、それぞれ独立して、単結合、置換若しくは非置換の(C6−C30)アリーレン又は置換若しくは非置換の(3〜30員)ヘテロアリーレンを表し、及び
前記ヘテロアリール(ヘテロアリーレン)は、B、N、O、S、Si及びPから選択される少なくとも1つのヘテロ原子を含有する)
によって表される少なくとも1つの化合物と
を含む有機エレクトロルミネセント材料。 - R1は、水素原子又は置換若しくは非置換の(C1−C6)アルキルを表し、
R2は、置換又は非置換の(C1−C6)アルキルを表し、
R3及びR5は、それぞれ独立して、置換若しくは非置換の(C1−C6)アルキル又は置換若しくは非置換の(C6−C18)アリールを表し、
R4は、水素、置換若しくは非置換の(C1−C6)アルキル又は置換若しくは非置換の(C6−C18)アリールを表し、
a及びbは、それぞれ独立して、1又は2を表し、ここで、a及びbがそれぞれ独立して2である場合、R1及びR2のそれぞれは、同一であるか又は異なり得る、請求項1に記載の有機エレクトロルミネセント材料。 - 式2は、下記の式3:
A環及びB環のいずれか一方は、置換又は非置換のナフタレン環を表し、且つ他方は、置換又は非置換のベンゼン環を表し、
X1〜X3は、それぞれ独立して、CR6又はNを表し、但し、X1〜X3の少なくとも1つは、Nを表し、
R6は、水素又は置換若しくは非置換の(C6−C30)アリールを表し、
Ar3は、水素、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)アリール又は置換若しくは非置換の(3〜30員)ヘテロアリールを表し、
cは、1〜4の整数を表し、ここで、cが2以上の整数である場合、Ar3のそれぞれは、同一であるか又は異なり得、及び
Ar1、L1及びL2は、請求項1に記載の通りである)
によって表される、請求項1に記載の有機エレクトロルミネセント材料。 - R1〜R5、Ar1、Ar2、L1、L2、A環及びB環における前記置換アルキル、前記置換アルケニル、前記置換アリール(アリーレン)、前記置換ヘテロアリール(ヘテロアリーレン)、前記置換ベンゼン環及び前記置換ナフタレン環の置換基は、それぞれ独立して、重水素、ハロゲン、シアノ、カルボキシル、ニトロ、ヒドロキシル、(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、(3〜7員)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、(C6−C30)アリール、(5〜30員)ヘテロアリール、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−又はジ−(C1−C30)アルキルアミノ、モノ−又はジ−(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)アリールからなる群から選択される少なくとも1つである、請求項1に記載の有機エレクトロルミネセント材料。
- 式1によって表される前記化合物は、
- 式2によって表される前記化合物は、
- 請求項1に記載の有機エレクトロルミネセント材料を含む有機エレクトロルミネセントデバイス。
- ドーパントとしての前記式1によって表される前記化合物と、ホストとしての前記式2によって表される前記化合物とを含む、請求項7に記載の有機エレクトロルミネセントデバイス。
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- 2017-12-05 EP EP17878052.4A patent/EP3551721A4/en not_active Withdrawn
- 2017-12-05 US US16/349,730 patent/US20190326525A1/en not_active Abandoned
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CN117946183A (zh) | 2024-04-30 |
EP3551721A1 (en) | 2019-10-16 |
JP7075402B2 (ja) | 2022-05-25 |
US20190326525A1 (en) | 2019-10-24 |
WO2018105986A1 (en) | 2018-06-14 |
EP3551721A4 (en) | 2020-07-01 |
CN109952358A (zh) | 2019-06-28 |
KR20180065353A (ko) | 2018-06-18 |
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