JP6502631B2 - 有機エレクトロルミネセンス材料、及びデバイス - Google Patents
有機エレクトロルミネセンス材料、及びデバイス Download PDFInfo
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- JP6502631B2 JP6502631B2 JP2014166272A JP2014166272A JP6502631B2 JP 6502631 B2 JP6502631 B2 JP 6502631B2 JP 2014166272 A JP2014166272 A JP 2014166272A JP 2014166272 A JP2014166272 A JP 2014166272A JP 6502631 B2 JP6502631 B2 JP 6502631B2
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- 239000000463 material Substances 0.000 title description 129
- 150000001875 compounds Chemical class 0.000 claims description 281
- 239000000203 mixture Substances 0.000 claims description 127
- 238000000151 deposition Methods 0.000 claims description 81
- 230000008021 deposition Effects 0.000 claims description 63
- -1 heteroalkenyl Chemical group 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 20
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 20
- 150000002527 isonitriles Chemical class 0.000 claims description 20
- 150000002825 nitriles Chemical class 0.000 claims description 20
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 20
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 20
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 18
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 238000001771 vacuum deposition Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 15
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
- 238000010549 co-Evaporation Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
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- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 5
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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 5
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- 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 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 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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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Description
本願は、米国特許法第119条(e)に基づき、その開示内容の全体を参照によって援用する、2014年2月17日出願の米国特許仮出願第61/940,603号、2013年12月24日出願の米国特許仮出願第61/920,544号、2013年10月22日出願の米国特許仮出願第61/894,160号、2013年9月6日出願の米国特許仮出願第61/874,444号、2013年8月20日出願の米国特許仮出願第61/867,858号、及び2014年4月15日出願の米国特許仮出願第14/253,505号、に対する優先権を主張するものである。
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、
前記有機層は、第1の化合物と第2の化合物との混合物を含む第1の組成物を更に含み、
前記第1の化合物は、前記第2の化合物と異なる化学構造を有し;
前記第1の化合物は、室温で、有機発光デバイス中でリン光発光体として機能することができ;
前記第1の化合物は、150℃〜350℃の蒸着温度T1を有し;
前記第2の化合物は、150℃〜350℃の蒸着温度T2を有し;
T1−T2の絶対値は、20℃未満であり;
前記混合物において前記第1の化合物は濃度C1を有し、前記混合物を、真空蒸着器具中、1×10−6Torr〜1×10−9Torrの一定圧力、及び蒸着速度2Å/秒で、蒸着される前記混合物から所定の距離だけ離れて位置する表面に蒸着することによって形成された膜において、前記第1の化合物は濃度C2を有し;前記(C1−C2)/C1の絶対値が5%未満である第1のデバイスが提供される。
前記方法は、
前記第1の電極をその上に配置されて有する基板を提供することと;
前記第1の電極上に、前記第1の組成物を堆積することと;
前記第1の有機層上に、前記第2の電極を堆積することと;
を含み、
前記第1の化合物は、前記第2の化合物と異なる化学構造を有し;
前記第1の化合物は、室温で、有機発光デバイス中のリン光発光体として機能することができ;
前記第1の化合物は、150℃〜350℃の蒸着温度T1を有し;
前記第2の化合物は、150℃〜350℃の蒸着温度T2を有し;
前記T1−T2の絶対値は、20℃未満であり:
前記第1の化合物は、前記混合物において前記第1の化合物は濃度C1を有し、前記混合物を、真空蒸着器具中、1×10−6Torr〜1×10−9Torrの一定圧力、及び蒸着速度2Å/秒で、蒸着される前記混合物から所定の距離だけ離れて位置する表面に蒸着することによって形成された膜において、前記第1の化合物は濃度C2を有し;前記T1−T2の絶対値が20℃未満である。
第1の実施例においては、非常に類似した昇華特性を有する、2つの発光体型化合物である化合物20及び化合物145の新規な組合せを互いに予混合し、単一の堆積源に載置して、様々な比率でデバイスEMLとして蒸着させた。例えば、これら2つの発光体の混合物を2000Å厚膜に、0.2Å/秒で堆積させた。一方で、材料を1Å/秒の蒸着速度で基板上に堆積させ、70nm厚膜を得た。混合前に重量基準で測定された、予混合物における2つの発光体の比は、85%(化合物20):15%(化合物145)であった。高速液体クロマトグラフィー(HPLC)で測定された予混合物の組成は、84.5%(化合物20):15.5%(化合物145)であった。混合は、予混合物全体において不均一性をもたらすことがあるので、少量の試料をHPLCで分析するとき、予混合物成分の測定された%に対して1%の誤差範囲が与えられる。HPLCで測定される、堆積された膜の組成は、85.3%(化合物20):14.7%(化合物145)であった。したがって、予混合物の組成と堆積された材料の組成とは、等価である。
これらのデータは、ホスト化合物H1、発光体化合物E5、これらの系統からの発光体及び潜在的な他のホストを、予混合し、PHOLEDのEMLの単一の蒸着源、又はEMLの部分として使用することができることを示す。
ホスト化合物EH40、及び発光体化合物97もまた、予混合性(premixability)を示す。これらの化合物は、構成を変えることなく予混合され、1つの蒸着源から共蒸着されうることを意味する。ホスト:発光体の組合せの均一な共蒸着は、この予混合された前駆体から作製されたデバイスの性能の一貫性にとって重要である。ホスト化合物EH40及び発光体化合物97の構造が下記に示される。
式中、L1、L2、及びL3は、同一であっても異なっていてもよく;
xは、1、2、又は3であり;
yは、0、1、又は2であり;
zは、0、1、又は2であり;
x+y+zは、前記金属Mの酸化状態であり;
L1、L2、及びL3は、独立して、下記からなる群から選択される。
Ra、Rb、Rc、及びRdは、独立して、水素、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、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、スルフォニル、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;且つ
Ra、Rb、Rc、及びRdのうちの2つの隣接する置換基は、結合して縮合環又は多座配位子を形成してもよい。
Re、Rf、Rh、及びRiのうち少なくとも1つは、少なくとも2つの炭素原子を有し;
Rgは、水素、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、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、スルフォニル、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。
RBは、モノ、ジ、トリ、テトラ置換を表すか、又は無置換であり;
RA、RB、RC、RD、及びREは、それぞれ独立して、水素、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、アリールアルキル、アルコキシ、アリールオキシ、アミノ、環状アミノ、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、スルフォニル、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;
nは、1又は2であり;
前記第2の化合物は、下記の式IIを有する:
Lは、直接的な結合、アリーレン、置換されたアリーレン、ヘテロアリーレン、置換されたヘテロアリーレン、及びこれらの組合せからなる群から選択され;
X1、X2、X3、X4、X5、X6、X7、Y1、Y2、及びY3は、それぞれ独立して、CR及びNからなる群から選択され;
Y1、Y2、及びY3の少なくとも2つは、Nであり;
それぞれのRは、同一であっても異なっていてもよく、且つ独立して、水素、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、アリールアルキル、アルコキシ、アリールオキシ、アミノ、環状アミノ、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、スルフォニル、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。
Raa、Rbb、Rcc、及びRddは、モノ、ジ、トリ、又はテトラ置換を表すか、無置換でよく;
Raa、Rbb、Rcc、及びRddは、独立して、水素、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、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、スルフォニル、ホスフィノ及びこれらの組合せからからなる群から選択され;
Raa、Rbb、Rcc、及びRddのうちの2つの隣接する置換基は、結合して縮合環又は多座配位子を形成してもよく;且つ
Rccの少なくとも1つは、五、六員炭素環、又は複素環である。
Yは、O、S、Se、NR’、及びCR’’R’’’からなる群から選択され;
L1は、単結合であるか、又は炭素原子5〜24個を有し、更に置換されていてもよいアリーレン基又はヘテロアリーレン基を含み;
Z1、Z2、Z3、Z4、及びZ5は、それぞれ独立して、CR’’’’及びNからなる群から選択され;
Z1、Z2、Z3、Z4、及びZ5の少なくとも1つはNであり;且つ
R11、R12、R’、R’’、R’’’、及びR’’’’は、それぞれ独立して、水素、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、スルフォニル、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;
前記第2の化合物は、下記の式VIを有する。
RCCは、それぞれ独立して、モノ、ジ、又はトリ置換を表すか、無置換であり;
RAA、RBB、RCC、RDD、及びREEは、独立して、水素、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、スルフォニル、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;
且つmは、1又は2である。
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、前記有機層は、第1の化合物及び第2の化合物との混合物を含み、前記第1の化合物は、前記第2の化合物と異なる化学構造を有し;
前記第1の化合物は、室温で、有機発光デバイス中でリン光発光体として機能することができ;
前記第1の化合物は、150℃〜350℃蒸着温度T1を有し;
前記第2の化合物は、150℃〜350℃の蒸着温度T2を有し;
T1−T2の絶対値は、20℃未満であり;
前記第1の化合物は、前記混合物中における前記第1の化合物の濃度がC1であり、前記混合物を真空蒸着器具において、1×10−6Torr〜1×10−9Torrの一定圧力、及び蒸着速度2Å/秒で、前記材料から既定義の距離から離れて位置する表面に前記混合物を蒸着することによって形成された膜における前記第1の化合物の濃度がC2であり;
前記(C1−C2)/C1の絶対値は、5%未満である第1のOLEDが提供され;且つ
前記(C1−C2)/C1の絶対値は、3%未満が好ましい。
前記第1の化合物は、前記第2の化合物と異なる化学構造を有し;
前記第1の化合物は、室温で、有機発光デバイス中のリン光発光体として機能することができ;
前記第1の化合物は、150℃〜350℃蒸着温度T1を有し;
前記第2の化合物は、150℃〜350℃の蒸着温度T2を有し;
T1−T2の絶対値は、20℃未満であり;
前記第1の化合物は、前記混合物中における前記第1の化合物の濃度がC1であり、前記混合物を真空蒸着器具において、1×10−6Torr〜1×10−9Torrの一定圧力、及び蒸着速度2Å/秒で、前記材料から既定義の距離から離れて位置する表面に前記混合物を蒸着することによって形成された膜における前記第1の化合物の濃度がC2であり;
前記(C1−C2)/C1の絶対値は、5%未満である。
他の材料との組合せ
HIL/HTL:
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。
式中、Metは、40より大きい原子量を有し得る金属であり;(Y101−Y102)は二座配位子であり、Y101及びY102は、C、N、O、P及びSから独立に選択され;L101は補助配位子であり;k’は、1から金属に付着し得る配位子の最大数までの整数値であり;且つ、k’+k’’は、金属に付着し得る配位子の最大数である。
ホスト:
HBL:
ETL:
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 (5)
- 第1の化合物と第2の化合物との混合物を含む組成物であって;
前記第1の化合物は、前記第2の化合物と異なる化学構造を有し;
前記第1の化合物は、室温で、有機発光デバイス中のリン光発光体として機能することができ;
前記第1の化合物は、150℃〜350℃の蒸着温度T1を有し;
前記第2の化合物は、150℃〜350℃の蒸着温度T2を有し;
T1−T2の絶対値は、20℃未満であり;
前記混合物中において前記第1の化合物は濃度C1を有し、前記混合物を、真空蒸着器具中、1×10−6Torr〜1×10−9Torrの一定圧力、及び蒸着速度2Å/秒で、蒸着される前記混合物から所定の距離だけ離れて位置する表面に蒸着することによって形成された膜において、前記第1の化合物は濃度C2を有し;且つ
前記(C1−C2)/C1の絶対値が5%未満であり、
前記第2の化合物が下記の式IIの構造を有することを特徴とする組成物。
Lは、直接的な結合であり;
X1、X2、X3、X4、X5、X6、X7、Y1、Y2、及びY3は、それぞれ独立して、CR及びNからなる群から選択され;
Y1、Y2、及びY3の少なくとも2つは、Nであり;且つ
それぞれのRは、同一であっても異なっていてもよく、且つ独立して、水素、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、アリールアルキル、アルコキシ、アリールオキシ、アミノ、環状アミノ、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、スルフォニル、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。)
(ただし、前記第2の化合物が、R 1 が水素である化合物である場合を除く。) - 第1の化合物が下記の式Iの構造を有する請求項1に記載の組成物。
RBは、モノ、ジ、トリ、テトラ置換を表すか、又は無置換であり;
RA、RB、RC、RD、及びREは、それぞれ独立して、水素、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、アリールアルキル、アルコキシ、アリールオキシ、アミノ、環状アミノ、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、スルフォニル、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;
nは、1又は2である。) - 第2の化合物が下記の式IIIの構造を有する請求項1から2のいずれかに記載の組成物。
- 第1の化合物が下記の式IVの構造を有する請求項2から3のいずれかに記載の組成物。
- 第2の化合物が下記のH1〜H7、及びH11〜H50からなる群から選択され、第1の化合物が下記のE1〜E40からなる群から選択される請求項1から4のいずれかに記載の組成物。
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EP3425693B1 (en) | 2023-04-26 |
KR20210057711A (ko) | 2021-05-21 |
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TWI647231B (zh) | 2019-01-11 |
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KR20220054768A (ko) | 2022-05-03 |
EP3425693A2 (en) | 2019-01-09 |
US20200335702A1 (en) | 2020-10-22 |
JP2019110303A (ja) | 2019-07-04 |
CN104419415A (zh) | 2015-03-18 |
US11611042B2 (en) | 2023-03-21 |
TWI709564B (zh) | 2020-11-11 |
TW201509947A (zh) | 2015-03-16 |
CN111662706A (zh) | 2020-09-15 |
US10074806B2 (en) | 2018-09-11 |
US10749114B2 (en) | 2020-08-18 |
EP2849240B1 (en) | 2018-09-19 |
JP2015041775A (ja) | 2015-03-02 |
US20150053939A1 (en) | 2015-02-26 |
JP6999772B2 (ja) | 2022-01-19 |
EP2849240A2 (en) | 2015-03-18 |
TW201927803A (zh) | 2019-07-16 |
JP2021010021A (ja) | 2021-01-28 |
EP3425693A3 (en) | 2019-05-01 |
KR102390440B1 (ko) | 2022-04-25 |
JP6779325B2 (ja) | 2020-11-04 |
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