JP7247121B2 - 有機電子デバイスのための組成物 - Google Patents
有機電子デバイスのための組成物 Download PDFInfo
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- JP7247121B2 JP7247121B2 JP2019572002A JP2019572002A JP7247121B2 JP 7247121 B2 JP7247121 B2 JP 7247121B2 JP 2019572002 A JP2019572002 A JP 2019572002A JP 2019572002 A JP2019572002 A JP 2019572002A JP 7247121 B2 JP7247121 B2 JP 7247121B2
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- 125000006836 terphenylene group Chemical group 0.000 description 1
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
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- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H10K30/353—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains comprising blocking layers, e.g. exciton blocking layers
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Description
Xは、出現する毎に、同一でまたは異なって、CRまたはNであり;
Vは、結合、C(R0)2、OまたはSであり;
vは、0または1であり;
X2は、出現する毎に、同一でまたは異なって、CR1またはNであり;
Zは、C(R0)2、NR1、OまたはSであり;
nは、0または1であり;
Ar1およびAr2は、各場合において、互いに独立に、芳香族環原子6~40個を有する芳香族環系または芳香族環原子10~40個を有するヘテロ芳香族環系(これらは、1以上のラジカルR3によって置換されていてもよい)であり;
R0は、出現する毎に、同一でまたは異なって、C原子1~4個を有する直鎖もしくは分枝アルキル基であるか、または両方のR0は、単環式もしくは多環式の、脂肪族、芳香族またはヘテロ芳香族環系(これらは、1以上のラジカルR2によって置換されていてもよい)を形成し;
Rは、出現する毎に、同一でまたは異なって、H、D、F、Cl、Br、I、CN、NO2、N(Ar)2、N(R2)2、C(=O)Ar、C(=O)R2、P(=O)(Ar)2、P(Ar)2、B(Ar)2、Si(Ar)3、Si(R2)3、C原子1~20個を有する直鎖アルキル、アルコキシもしくはチオアルキル基、またはC原子3~20個を有する分枝もしくは環状アルキル、アルコキシもしくはチオアルキル基、またはC原子2~20個を有するアルケニル基(これらは、各場合において、1以上のラジカルR2によって置換されていてもよい)(ここで、1以上の隣接していないCH2基は、R2C=CR2、Si(R2)2、C=O、C=S、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2によって置きかえられていてもよく、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2によって置きかえられていてもよい)、芳香環原子5~40個を有する芳香族もしくはヘテロ芳香族環系(これらは、各場合において、1以上のラジカルR2によって置換されていてもよい)、または芳香環原子5~40個を有するアリールオキシもしくはヘテロアリールオキシ基(これらは、1以上のラジカルR2によって置換されていてもよい)、または芳香環原子5~40個を有するアラルキルもしくはヘテロアラルキル基(これらは、1以上のラジカルR2によって置換されていてもよい)からなる群から選択され;同じ炭素原子または隣接している炭素原子に結合している2つの置換基Rは、単環式もしくは多環式の、脂肪族、芳香族またはヘテロ芳香族環系(これらは、1以上のラジカルR2によって置換されていてもよい)を任意に形成していてもよく;
R1は、出現する毎に、同一でまたは異なって、H、D、F、Cl、Br、I、CN、NO2、N(Ar)2、N(R2)2、C(=O)Ar、C(=O)R2、P(=O)(Ar)2、P(Ar)2、B(Ar)2、Si(Ar)3、Si(R2)3、C原子1~20個を有する直鎖アルキル、アルコキシもしくはチオアルキル基、またはC原子3~20個を有する分枝もしくは環状アルキル、アルコキシもしくはチオアルキル基、またはC原子2~20個を有するアルケニル基(これらは、各場合において、1以上のラジカルR2によって置換されていてもよい)(ここで、1以上の隣接していないCH2基は、R2C=CR2、Si(R2)2、C=O、C=S、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2によって置きかえられていてもよく、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2によって置きかえられていてもよい)、芳香環原子5~40個を有する芳香族もしくはヘテロ芳香族環系(これらは、各場合において、1以上のラジカルR2によって置換されていてもよい)、または芳香環原子5~40個を有するアリールオキシもしくはヘテロアリールオキシ基(これらは、1以上のラジカルR2によって置換されていてもよい)、または芳香環原子5~40個を有するアラルキルもしくはヘテロアラルキル基(これらは、1以上のラジカルR2によって置換されていてもよい)からなる群から選択され;
R2は、出現する毎に、同一でまたは異なって、H、D、F、Cl、Br、I、CN、NO2、N(Ar)2、NH2、N(R3)2、C(=O)Ar、C(=O)H、C(=O)R3、P(=O)(Ar)2、C原子1~40個を有する直鎖アルキル、アルコキシもしくはチオアルキル基、またはC原子3~40個を有する分枝もしくは環状アルキル、アルコキシもしくはチオアルキル基、またはC原子2~40個を有するアルケニルもしくはアルキニル基(これらは、各場合において、1以上のラジカルR3によって置換されていてもよい)(ここで、1以上の隣接していないCH2基は、HC=CH、R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NH、NR3、O、S、CONHもしくはCONR3によって置きかえられていてもよく、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2によって置きかえられていてもよい)、芳香環原子5~60個を有する芳香族もしくはヘテロ芳香族環系(これらは、各場合において、1以上のラジカルR3によって置換されていてもよい)、または芳香環原子5~60個を有するアリールオキシもしくはヘテロアリールオキシ基(これらは、1以上のラジカルR3によって置換されていてもよい)、またはこれらの系の組み合わせからなる群から選択され、ここで、2以上の隣接している置換基R2は、単環式もしくは多環式の、脂肪族、芳香族またはヘテロ芳香族環系(これらは、1以上のラジカルR3によって置換されていてもよい)を任意に形成していてもよく;
R3は、出現する毎に、同一でまたは異なって、H、D、F、CN、C原子1~20個を有する脂肪族炭化水素ラジカル、または環原子6~30個を有する芳香族環系、または環原子10~30個を有するヘテロ芳香族環系(ここで、1以上のH原子は、D、F、Cl、Br、IもしくはCNによって置きかえられていてもよく、それぞれ炭素原子1~4個を有する1以上のアルキル基によって置換されていてもよい)からなる群から選択され;2以上の隣接している置換基R3は、互いと、単環式もしくは多環式の脂肪族環系を形成していてもよく;
Arは、出現する毎に、同一でまたは異なって、芳香族環原子5~30個を有する芳香族もしくはヘテロ芳香族環系(これらは、1以上の非芳香族ラジカルR3によって置換されていてもよい)であり;同じN原子、P原子またはB原子に結合している2つのラジカルArはまた、単結合、またはN(R3)、C(R3)2、OもしくはSから選択される架橋によって互いに架橋されていてもよい]
に関する。
によって記載される。
に相当する、上に記載の組成物に関する。
から選択される。
に相当する。
に相当する。
に相当する。
に相当する。Vは、特に好ましくは、C(R0)2であり、ここで、R0は、各場合において、互いに独立に、上記に示す意味を有する。
である。
である。
である。
である。
によって表される。
によって表される。
によって表される。
E(T1(eV))=1240/E(T1(nm))=1240/Plmax.(nm)
したがって、好ましい燐光エミッターは、三重項エネルギーT1が、好ましくは、約1.9eV~約1.0eVである、好ましくは表5または6からの赤外線エミッターである。
アノード/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/カソード
この層の順序が、好ましい順序である。
軌道エネルギーおよび電子状態の決定
材料の、HOMOおよびLUMOエネルギー、ならびに三重項準位および一重項準位は、量子化学計算によって決定される。この目的で、「Gaussian09、Revision D.01」ソフトウェアパッケージ(Gaussian Inc.)が本出願において使用される。金属を除く有機物質の計算のために(「org.」方法によって示される)、最初に、構造最適化は、電荷0および多重度1で、半経験的な方法であるAM1(Gaussian input line「# AM1 opt」)を使用して行われる。これに続いて、最適化された構造に基づいて、電子基底状態および三重項準位のためのエネルギー計算(単一ポイント)が行われる。ここで、6-31G(d)基底集合(Gaussian input line「# B3PW91/6-31G(d) td=(50-50,nstates=4)」)を用いるTDDFT(時間依存密度汎関数理論)方法であるB3PW91を使用する(電荷0、多重度1)。有機金属化合物(「org.-m」方法によって示される)のために、構造は、Hartree-Fock方法およびLanL2MB基底集合(Gaussian input line「# HF/LanL2MB opt」)を使用して最適化される(電荷0、多重度1)。エネルギー計算は、「LanL2DZ」基底集合が金属原子のために使用され、「6-31G(d)」基底集合が配位子のために使用されるという相違により、上に記載のようにして、有機物質と同様に行われる(Gaussian input line「#B3PW91/gen pseudo=lanl2 td=(50-50,nstates=4)」)。エネルギー計算は、ハートリー単位で、2個の電子によって占有される最後の軌道としてHOMO(Alpha occ.固有値)および最初の未占有軌道としてLUMO(Alpha virt.固有値)を与え、ここで、HEhおよびLEhは、ハートリー単位のHOMOエネルギー、およびハートリー単位のLUMOエネルギーをそれぞれ表す。サイクリックボルタンメトリー測定を参照して補正された電子ボルトのHOMOおよびLUMO値は、以下のようにして、これらから決定される。
HOMO(eV)=(HEh×27.212)×0.8308-1.118
LUMO(eV)=(LEh×27.212)×1.0658-0.5049
材料の三重項状態T1は、量子化学エネルギー計算から生じる最低エネルギーを有する三重項状態の相対励起エネルギー(eV)として定義される。
OLEDにおける本発明による材料の組み合わせの使用を下記の例E1、E2、E3およびE4に提示する(表7を参照のこと)。
本発明による材料の組み合わせは、燐光OLEDにおける発光層中で利用することができる。化合物L2と、BisCbz1(化合物B14に相当する)との本発明による組み合わせが、発光層中のマトリックス材料として、例E1およびE2において利用される。化合物L2とBisCbz2(化合物B3に相当する)との本発明による組み合わせが、発光層中のマトリックス材料として、例E3およびE4において利用される。
化合物L1は、文献から公知であり、WO2014/094964の58および59頁の合成例1と同様に調製される。
化合物B14は、文献から公知であり、WO2010/136109の133および134頁の例50と同様に調製される。
Claims (18)
- 少なくとも1つの式(1a)の化合物および少なくとも1つの式(2)の化合物を含む組成物。
Vは、結合であり;
vは、1であり;
X2は、出現する毎に、同一でまたは異なって、CR1であり;
nは、0であり;
Ar1およびAr2は、各場合において、互いに独立に、芳香族環原子6~40個を有する芳香族環系または芳香族環原子10~40個を有するヘテロ芳香族環系であり、ここで、ヘテロ芳香族環系は、全部で1個のN原子のみを含有するか、または、全部で1以上のOおよび/またはS原子を含有し;
Rは、出現する毎に、同一でまたは異なって、H、芳香環原子5~40個を有する芳香族もしくはヘテロ芳香族環系からなる群から選択され;同じ炭素原子または隣接している炭素原子に結合している2つの置換基Rは、単環式もしくは多環式の、脂肪族、芳香族またはヘテロ芳香族環系を任意に形成していてもよく;
R1は、出現する毎に、同一でまたは異なって、Hまたは芳香環原子5~40個を有する芳香族もしくはヘテロ芳香族環系からなる群から選択され、このR1中の芳香環原子5~40個を有する芳香族またはヘテロ芳香族環系は、ベンゼン、ジベンゾフラン、ジベンゾチオフェン、9-フェニルカルバゾール、ビフェニルまたはテルフェニルから誘導される。] - 前記置換基Ar1およびAr2の1つが、芳香環原子6~40個を有する芳香族環系、または芳香環原子10~40個を有するヘテロ芳香族系を示し、ここで、ヘテロ芳香族環系は、全部で1個のN原子のみを含有するか、または、全部で1以上のOおよび/またはS原子を含有し;他の置換基が、芳香環原子6~40個を有する芳香族環系を示すことを特徴とする、請求項1に記載の組成物。
- 前記置換基Ar1またはAr2が、各場合において、互いに独立に、芳香環原子6~40個を有する芳香族環系を示すことを特徴とする、請求項1に記載の組成物。
- 前記組成物が、正孔注入材料、正孔輸送材料、正孔阻止材料、ワイドバンドギャップ材料、蛍光エミッター、燐光エミッター、ホスト材料、電子阻止材料、電子輸送材料および電子注入材料、n-ドーパントおよびp-ドーパントからなる群から選択される少なくとも1つのさらなる化合物を含むことを特徴とする、請求項1に記載の組成物。
- 請求項1~6の何れか1項に記載の組成物、および少なくとも1つの溶媒を含む調合物。
- 有機電子デバイスにおける、請求項1~6の何れか1項に記載の組成物の使用。
- 前記有機電子デバイスが、有機集積回路(OIC)、有機電界効果トランジスタ(OFET)、有機薄膜トランジスタ(OTFT)、有機エレクトロルミネッセンスデバイス、有機ソーラーセル(OSC)、有機光学検出器および有機光受容器の群から選択されることを特徴とする、請求項8に記載の使用。
- 請求項1~6の何れか1項に記載の少なくとも1つの組成物を含有する、有機電子デバイス。
- 有機集積回路(OIC)、有機電界効果トランジスタ(OFET)、有機薄膜トランジスタ(OTFT)、有機エレクトロルミネッセンスデバイス、有機ソーラーセル(OSC)、有機光学検出器および有機光受容器の群から選択されることを特徴とする、請求項10に記載のデバイス。
- 有機発光トランジスタ(OLET)、有機電場消光デバイス(OFQD)、有機発光電気化学セル(OLEC、LEC、LEEC)、有機レーザーダイオード(O-laser)および有機発光ダイオード(OLED)から選択されるエレクトロルミネッセンスデバイスであることを特徴とする、請求項10に記載のデバイス。
- 発光層(EML)中、電子輸送層(ETL)中、電子注入層(EIL)中および/または正孔阻止層(HBL)中に請求項1~6の何れか1項に記載の組成物を含有することを特徴とする、請求項10に記載のデバイス。
- 発光層中に、燐光エミッターと一緒に請求項1~6の何れか1項に記載の組成物を含有することを特徴とする、請求項10に記載のデバイス。
- 請求項1~6の何れか1項に記載の組成物を含む少なくとも1つの有機層が、気相堆積によってまたは溶液から適用されることを特徴とする、請求項10に記載のデバイスの製造のための方法。
- 請求項1~6のうちの1項に記載した通りの前記少なくとも1つの式(1)の化合物および前記少なくとも1つの式(2)の化合物が、任意にさらなる材料とともに、少なくとも2つの材料源から、連続してまたは同時に、気相から堆積され、有機層を形成することを特徴とする、請求項15に記載の方法。
- 請求項1~6の何れか1項に記載の組成物が、気相堆積のための材料源として利用され、有機層を形成することを特徴とする、請求項15に記載の方法。
- 請求項7に記載の調合物が、有機層を適用するために使用されることを特徴とする、請求項15に記載の方法。
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US20200216391A1 (en) | 2020-07-09 |
JP2020526026A (ja) | 2020-08-27 |
TW201920101A (zh) | 2019-06-01 |
KR20200024907A (ko) | 2020-03-09 |
EP3649213A1 (de) | 2020-05-13 |
KR102653984B1 (ko) | 2024-04-02 |
WO2019007867A1 (de) | 2019-01-10 |
CN110832053A (zh) | 2020-02-21 |
TWI768075B (zh) | 2022-06-21 |
EP3649213B1 (de) | 2021-06-23 |
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