JP2019069938A - エレクトロルミネセンスデバイスのための有機ホスト材料 - Google Patents
エレクトロルミネセンスデバイスのための有機ホスト材料 Download PDFInfo
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- JP2019069938A JP2019069938A JP2018176054A JP2018176054A JP2019069938A JP 2019069938 A JP2019069938 A JP 2019069938A JP 2018176054 A JP2018176054 A JP 2018176054A JP 2018176054 A JP2018176054 A JP 2018176054A JP 2019069938 A JP2019069938 A JP 2019069938A
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- aryl
- heteroaryl
- substituted
- organic
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- 239000000463 material Substances 0.000 title claims description 88
- 238000005401 electroluminescence Methods 0.000 title 1
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- 239000010410 layer Substances 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 57
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
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- 125000003342 alkenyl group Chemical group 0.000 claims description 25
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- 238000006467 substitution reaction Methods 0.000 claims description 25
- 239000002019 doping agent Substances 0.000 claims description 24
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- 239000001257 hydrogen Substances 0.000 claims description 24
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- 239000000243 solution Substances 0.000 description 6
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- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000010129 solution processing Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
- HWIATMHDQVGMFQ-UHFFFAOYSA-N 1,3-azaborinine Chemical compound B1=CC=CN=C1 HWIATMHDQVGMFQ-UHFFFAOYSA-N 0.000 description 1
- VRVRKVMNULDZPO-UHFFFAOYSA-N 1,3-oxazole;1,3-thiazole Chemical compound C1=COC=N1.C1=CSC=N1 VRVRKVMNULDZPO-UHFFFAOYSA-N 0.000 description 1
- OBUDOIAYABJUHQ-UHFFFAOYSA-N 1,4-azaborinine Chemical compound B1=CC=NC=C1 OBUDOIAYABJUHQ-UHFFFAOYSA-N 0.000 description 1
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- GPGGOIGDVKWSLJ-UHFFFAOYSA-N 5-phenyl-11h-indolo[3,2-b]carbazole Chemical compound C1=CC=CC=C1N1C2=CC(C3=CC=CC=C3N3)=C3C=C2C2=CC=CC=C21 GPGGOIGDVKWSLJ-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
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- 101150049278 US20 gene Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 125000002355 alkine group Chemical group 0.000 description 1
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- KCQLSIKUOYWBAO-UHFFFAOYSA-N azaborinine Chemical compound B1=NC=CC=C1 KCQLSIKUOYWBAO-UHFFFAOYSA-N 0.000 description 1
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- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
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- 229920001940 conductive polymer Polymers 0.000 description 1
- 150000004292 cyclic ethers Chemical class 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
- 238000007872 degassing Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- QPJFIVIVOOQUKD-UHFFFAOYSA-N dipyrazino[2,3-f:2,3-h]quinoxaline Chemical group C1=CN=C2C3=NC=CN=C3C3=NC=CN=C3C2=N1 QPJFIVIVOOQUKD-UHFFFAOYSA-N 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical compound C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 description 1
- RIYPENPUNLHEBK-UHFFFAOYSA-N phenanthro[9,10-b]pyridine Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 RIYPENPUNLHEBK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004585 polycyclic heterocycle group Chemical group 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012552 review 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
- 239000004065 semiconductor Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 125000006837 triphenylylene group Chemical group 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000012056 up-stream process Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- 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
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Abstract
Description
本願は、その開示内容の全体を参照によって組み込まれる、2017年10月5日出願の米国特許仮出願第62/568,570号に対する優先権を主張するものである。
Ra、Rb、Rc、及びRdは、それぞれ、モノ置換から置換の可能な最大数を表す、又は無置換を表してもよく;
R’、R’’、Ra、Rb、Rc、及びRdは、それぞれ独立して、水素である、又は重水素、ハライド、アルキル、シクロアルキル、ヘテロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボニル、カルボン酸、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルホニル、ホスフィノ、及びこれらの組合せからなる群から選択される置換基であり;
Ra、Rb、Rc、及びRdの任意の2つの隣接する置換基は、縮合又は結合して環を形成する、又は多座配位子を形成してもよい。
他の材料との組合せ
伝導性(導電性)ドーパント:
EP01617493、EP01968131、EP2020694、EP2684932、US20050139810、US20070160905、US20090167167、US2010288362、WO06081780、WO2009003455、WO2009008277、WO2009011327、WO2014009310、US2007252140、US2015060804、US20150123047、及びUS2012146012
式中、kは1から20までの整数であり;X101からX108はC(CHを含む)又はNであり;Z101はNAr1、O、又はSであり;Ar1は、上記で定義したものと同じ基を有する。
CN102702075、DE102012005215、EP01624500、EP01698613、EP01806334、EP01930964、EP01972613、EP01997799、EP02011790、EP02055700、EP02055701、EP1725079、EP2085382、EP2660300、EP650955、JP07−073529、JP2005112765、JP2007091719、JP2008021687、JP2014−009196、KR20110088898、KR20130077473、TW201139402、US06517957、US20020158242、US20030162053、US20050123751、US20060182993、US20060240279、US20070145888、US20070181874、US20070278938、US20080014464、US20080091025、US20080106190、US20080124572、US20080145707、US20080220265、US20080233434、US20080303417、US2008107919、US20090115320、US20090167161、US2009066235、US2011007385、US20110163302、US2011240968、US2011278551、US2012205642、US2013241401、US20140117329、US2014183517、US5061569、US5639914、WO05075451、WO07125714、WO08023550、WO08023759、WO2009145016、WO2010061824、WO2011075644、WO2012177006、WO2013018530、WO2013039073、WO2013087142、WO2013118812、WO2013120577、WO2013157367、WO2013175747、WO2014002873、WO2014015935、WO2014015937、WO2014030872、WO2014030921、WO2014034791、WO2014104514、WO2014157018
追加のホスト:
EP2034538、EP2034538A、EP2757608、JP2007254297、KR20100079458、KR20120088644、KR20120129733、KR20130115564、TW201329200、US20030175553、US20050238919、US20060280965、US20090017330、US20090030202、US20090167162、US20090302743、US20090309488、US20100012931、US20100084966、US20100187984、US2010187984、US2012075273、US2012126221、US2013009543、US2013105787、US2013175519、US2014001446、US20140183503、US20140225088、US2014034914、US7154114、WO2001039234、WO2004093207、WO2005014551、WO2005089025、WO2006072002、WO2006114966、WO2007063754、WO2008056746、WO2009003898、WO2009021126、WO2009063833、WO2009066778、WO2009066779、WO2009086028、WO2010056066、WO2010107244、WO2011081423、WO2011081431、WO2011086863、WO2012128298、WO2012133644、WO2012133649、WO2013024872、WO2013035275、WO2013081315、WO2013191404、WO2014142472、US20170263869、US20160163995、US9466803
CN103694277、CN1696137、EB01238981、EP01239526、EP01961743、EP1239526、EP1244155、EP1642951、EP1647554、EP1841834、EP1841834B、EP2062907、EP2730583、JP2012074444、JP2013110263、JP4478555、KR1020090133652、KR20120032054、KR20130043460、TW201332980、US06699599、US06916554、US20010019782、US20020034656、US20030068526、US20030072964、US20030138657、US20050123788、US20050244673、US2005123791、US2005260449、US20060008670、US20060065890、US20060127696、US20060134459、US20060134462、US20060202194、US20060251923、US20070034863、US20070087321、US20070103060、US20070111026、US20070190359、US20070231600、US2007034863、US2007104979、US2007104980、US2007138437、US2007224450、US2007278936、US20080020237、US20080233410、US20080261076、US20080297033、US200805851、US2008161567、US2008210930、US20090039776、US20090108737、US20090115322、US20090179555、US2009085476、US2009104472、US20100090591、US20100148663、US20100244004、US20100295032、US2010102716、US2010105902、US2010244004、US2010270916、US20110057559、US20110108822、US20110204333、US2011215710、US2011227049、US2011285275、US2012292601、US20130146848、US2013033172、US2013165653、US2013181190、US2013334521、US20140246656、US2014103305、US6303238、US6413656、US6653654、US6670645、US6687266、US6835469、US6921915、US7279704、US7332232、US7378162、US7534505、US7675228、US7728137、US7740957、US7759489、US7951947、US8067099、US8592586、US8871361、WO06081973、WO06121811、WO07018067、WO07108362、WO07115970、WO07115981、WO08035571、WO2002015645、WO2003040257、WO2005019373、WO2006056418、WO2008054584、WO2008078800、WO2008096609、WO2008101842、WO2009000673、WO2009050281、WO2009100991、WO2010028151、WO2010054731、WO2010086089、WO2010118029、WO2011044988、WO2011051404、WO2011107491、WO2012020327、WO2012163471、WO2013094620、WO2013107487、WO2013174471、WO2014007565、WO2014008982、WO2014023377、WO2014024131、WO2014031977、WO2014038456、WO2014112450
ETL:
実験
110 基板
115 アノード
120 正孔注入層
125 正孔輸送層
130 電子ブロッキング層
135 発光層
140 正孔ブロッキング層
145 電子輸送層
150 電子注入層
155 保護層
160 カソード
162 第一の導電層
164 第二の導電層
170 バリア層
200 反転させたOLED、デバイス
210 基板
215 カソード
220 発光層
225 正孔輸送層
230 アノード
Claims (15)
- 下記の式Iで表される化合物。
X1〜X4の2つは炭素であり、他の2つは窒素であり;
Lは、有機リンカーであり;
R、RA、RB、RC、及びRDは、それぞれ独立して、水素である、又は重水素、ハロゲン、アルキル、シクロアルキル、ヘテロアルキル、ヘテロシクロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボン酸、エーテル、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルホニル、ホスフィノ、及びこれらの組合せからなる群から選択される置換基であり;
RDは、ジベンゾチオフェン基を含まず;
任意の隣接する置換基は、結合又は縮合して環になっていてもよい。) - R、RA、RB、RC、及びRDが、それぞれ独立して、重水素、フッ素、アルキル、シクロアルキル、ヘテロアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アリール、ヘテロアリール、ニトリル、イソニトリル、スルファニル、及びこれらの組合せからなる群から選択される置換基である請求項1に記載の化合物。
- R、RA、RB、RC、及びRDが、それぞれ独立して、アリール、置換されたアリール、ヘテロアリール、置換されたヘテロアリール、アミノ、シリル、及びこれらの組合せからなる群から選択される置換基である請求項1に記載の化合物。
- Rが、置換又は非置換の6員芳香族環である請求項1に記載の化合物。
- RA、RB、及びRCが、水素である請求項1に記載の化合物。
- Lが、アリール、置換されたアリール、ヘテロアリール、置換されたヘテロアリール、アミノ、シリル、及びこれらの組合せからなる群から選択される請求項1に記載の化合物。
- Lが、置換又は非置換の6員芳香族環である請求項1に記載の化合物。
- RDが、置換又は非置換のアリールである請求項1に記載の化合物。
- 前記化合物が、下記からなる群から選択される請求項1に記載の化合物。
- 前記化合物が、下記からなる群から選択される請求項1に記載の化合物。
- アノードと;
カソードと;
前記アノードと前記カソードとの間に配置された有機層と、を含み、前記有機層が、下記の式Iで表される化合物を含むことを特徴とする有機発光デバイス(OLED)。
X1〜X4の2つは炭素であり、他の2つは窒素であり;
Lは、有機リンカーであり;
R、RA、RB、RC、及びRDは、それぞれ独立して、水素である、又は重水素、ハロゲン、アルキル、シクロアルキル、ヘテロアルキル、ヘテロシクロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボン酸、エーテル、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルホニル、ホスフィノ、及びこれらの組合せからなる群から選択される置換基であり;
RDは、ジベンゾチオフェン基を含まず;
任意の隣接する置換基は、結合又は縮合して環になっていてもよい。) - 前記有機層が、リン光発光ドーパントを更に含み;前記発光ドーパントが、下記からなる群から選択される少なくとも1つの配位子を有する、又は前記配位子が二座超である場合にはその一部を有する遷移金属錯体である請求項11に記載のOLED。
Ra、Rb、Rc、及びRdは、それぞれ、モノ置換から置換の可能な最大数を表す、又は無置換を表してもよく;
R’、R’’、Ra、Rb、Rc、及びRdは、それぞれ独立して、水素である、又は重水素、ハライド、アルキル、シクロアルキル、ヘテロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボニル、カルボン酸、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルホニル、ホスフィノ、及びこれらの組合せからなる群から選択される置換基であり;
Ra、Rb、Rc、及びRdの任意の2つの隣接する置換基は、縮合又は結合して環を形成する、又は多座配位子を形成してもよい。) - 前記有機層が、発光層であり、式Iで表される化合物が、ホストである;又は
前記有機層が、ブロッキング層であり、式Iで表される化合物が、前記有機層中のブロッキング材料である;又は
前記有機層が、輸送層であり、式Iで表される化合物が、前記有機層中の輸送材料である請求項11に記載のOLED。 - 有機発光デバイスを含む消費者製品であって、前記有機発光デバイスが、
アノードと;
カソードと;
前記アノードと前記カソードとの間に配置された有機層と、を含み、前記有機層が、下記の式Iで表される化合物を含むことを特徴とする消費者製品。
X1〜X4の2つは炭素であり、他の2つは窒素であり;
Lは、有機リンカーであり;
R、RA、RB、RC、及びRDは、それぞれ独立して、水素である、又は重水素、ハロゲン、アルキル、シクロアルキル、ヘテロアルキル、ヘテロシクロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボン酸、エーテル、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルホニル、ホスフィノ、及びこれらの組合せからなる群から選択される置換基であり;
RDは、ジベンゾチオフェン基を含まず;
任意の隣接する置換基は、結合又は縮合して環になっていてもよい。) - 前記消費者製品が、フラットパネルディスプレイ、曲がったディスプレイ、コンピュータモニター、メディカルモニター、テレビ、掲示板、屋内若しくは屋外照明及び/又は信号送信用のライト、ヘッドアップディスプレイ、完全又は部分透明ディスプレイ、フレキシブルディスプレイ、丸めることができるディスプレイ、折り畳むことができるディスプレイ、伸ばすことができるディスプレイ、レーザープリンター、電話、携帯電話、タブレット、ファブレット、パーソナルデジタルアシスタント(PDA)、ウェアラブルデバイス、ラップトップコンピュータ、デジタルカメラ、カムコーダー、ビューファインダー、対角で2インチ未満であるマイクロディスプレイ、3−Dディスプレイ、バーチャルリアリティ又は拡張現実ディスプレイ、車両、共に並べた多重ディスプレイを含むビデオウォール(video wall)、劇場又はスタジアムのスクリーン、光療法デバイス、及び看板の中の1つである請求項14に記載の消費者製品。
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014105209A (ja) * | 2012-11-26 | 2014-06-09 | Universal Display Corp | 遅延蛍光を示す有機発光化合物 |
JP2014518900A (ja) * | 2011-06-09 | 2014-08-07 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電子材料用の新規な化合物および同化合物を使用した有機電界発光素子 |
CN104245690A (zh) * | 2012-04-10 | 2014-12-24 | 罗门哈斯电子材料韩国有限公司 | 新有机电致发光化合物和包含该化合物的有机电致发光器件 |
WO2016195441A1 (ko) * | 2015-06-03 | 2016-12-08 | 주식회사 엘지화학 | 함질소 축합고리 화합물 및 이를 이용한 유기 발광 소자 |
KR20170099476A (ko) * | 2016-02-24 | 2017-09-01 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
WO2017183859A1 (en) * | 2016-04-18 | 2017-10-26 | Rohm And Haas Electronic Materials Korea Ltd. | A plurality of host materials and organic electroluminescent device comprising the same |
WO2018174678A1 (ko) * | 2017-03-24 | 2018-09-27 | 희성소재(주) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI666803B (zh) * | 2014-09-17 | 2019-07-21 | 日商日鐵化學材料股份有限公司 | 有機電場發光元件及其製造方法 |
KR102479135B1 (ko) * | 2016-04-18 | 2022-12-21 | 롬엔드하스전자재료코리아유한회사 | 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자 |
KR20180108425A (ko) * | 2017-03-24 | 2018-10-04 | 희성소재 (주) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR101943428B1 (ko) * | 2017-03-24 | 2019-01-30 | 엘티소재주식회사 | 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물 |
US10944060B2 (en) * | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
-
2018
- 2018-09-11 US US16/127,444 patent/US20190109286A1/en active Pending
- 2018-09-20 JP JP2018176054A patent/JP2019069938A/ja active Pending
- 2018-09-28 CN CN201811137049.6A patent/CN109651374A/zh active Pending
- 2018-10-02 KR KR1020180117617A patent/KR20190039652A/ko active Application Filing
-
2023
- 2023-02-14 JP JP2023020401A patent/JP2023078121A/ja active Pending
- 2023-09-19 KR KR1020230125048A patent/KR20230136585A/ko not_active Application Discontinuation
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014518900A (ja) * | 2011-06-09 | 2014-08-07 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電子材料用の新規な化合物および同化合物を使用した有機電界発光素子 |
CN104245690A (zh) * | 2012-04-10 | 2014-12-24 | 罗门哈斯电子材料韩国有限公司 | 新有机电致发光化合物和包含该化合物的有机电致发光器件 |
JP2014105209A (ja) * | 2012-11-26 | 2014-06-09 | Universal Display Corp | 遅延蛍光を示す有機発光化合物 |
WO2016195441A1 (ko) * | 2015-06-03 | 2016-12-08 | 주식회사 엘지화학 | 함질소 축합고리 화합물 및 이를 이용한 유기 발광 소자 |
KR20170099476A (ko) * | 2016-02-24 | 2017-09-01 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
WO2017183859A1 (en) * | 2016-04-18 | 2017-10-26 | Rohm And Haas Electronic Materials Korea Ltd. | A plurality of host materials and organic electroluminescent device comprising the same |
WO2018174678A1 (ko) * | 2017-03-24 | 2018-09-27 | 희성소재(주) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
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JP2023078121A (ja) | 2023-06-06 |
KR20230136585A (ko) | 2023-09-26 |
US20190109286A1 (en) | 2019-04-11 |
KR20190039652A (ko) | 2019-04-15 |
CN109651374A (zh) | 2019-04-19 |
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