JP6356060B2 - 有機イオン性機能材料 - Google Patents
有機イオン性機能材料 Download PDFInfo
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- JP6356060B2 JP6356060B2 JP2014500269A JP2014500269A JP6356060B2 JP 6356060 B2 JP6356060 B2 JP 6356060B2 JP 2014500269 A JP2014500269 A JP 2014500269A JP 2014500269 A JP2014500269 A JP 2014500269A JP 6356060 B2 JP6356060 B2 JP 6356060B2
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- olec
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- 239000008204 material by function Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 141
- -1 heterocyclic cation Chemical class 0.000 claims description 74
- 239000000463 material Substances 0.000 claims description 73
- 150000008040 ionic compounds Chemical class 0.000 claims description 55
- 239000011159 matrix material Substances 0.000 claims description 39
- 150000001450 anions Chemical class 0.000 claims description 34
- 238000002347 injection Methods 0.000 claims description 28
- 239000007924 injection Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000002500 ions Chemical class 0.000 claims description 21
- 150000002894 organic compounds Chemical class 0.000 claims description 18
- 150000001768 cations Chemical class 0.000 claims description 17
- 230000005525 hole transport Effects 0.000 claims description 16
- 125000000962 organic group Chemical group 0.000 claims description 16
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 6
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 5
- 150000001449 anionic compounds Chemical class 0.000 claims description 5
- 150000001767 cationic compounds Chemical class 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 3
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- 238000005516 engineering process Methods 0.000 description 8
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- 125000005843 halogen group Chemical group 0.000 description 8
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- 125000001072 heteroaryl group Chemical group 0.000 description 7
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- 125000000129 anionic group Chemical group 0.000 description 6
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical group 0.000 description 1
- 150000003567 thiocyanates Chemical group 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 210000002105 tongue Anatomy 0.000 description 1
- 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 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 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
- 230000009385 viral infection Effects 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- A61N2005/065—Light sources therefor
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- H10K50/135—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising mobile ions
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Description
Ar4、Ar5、Ar6は、出現毎に同一であるか異なり、モノもしくはポリ環式の芳香族もしくは複素環式芳香族環構造であって、6〜50個の炭素原子を有する置換もしくは非置換芳香族炭化水素環状基、5〜50個の非水素原子を有する置換もしくは非置換芳香族ヘテロ環状基、1〜50個の炭素原子を有する置換もしくは非置換アルキル基、3〜50個の核炭素原子を有する置換もしくは非置換シクロアルキル基、1〜50個の炭素原子を有する置換もしくは非置換アルコキシ基、6〜50個の炭素原子を有する置換もしくは非置換アラルキル基、5〜50個の炭素原子を有する置換もしくは非置換アリールオキシ基、5〜50個の炭素原子を有する置換もしくは非置換アリールチオ基、1〜50個の炭素原子を有する置換もしくは非置換アルコキシカルボニル基、1〜50個の炭素原子を有する置換もしくは非置換シリル基、カルボキシ基、ハロゲン原子、シアノ基、ニトロ基またはヒドロキシ基から選ばれる一以上の置換基により置換されてよい。
Ar4、Ar5およびAr6中のΠ電子の合計は、p=1ならば少なくとも30であり、p=2ならば少なくとも36であり、p=3ならば少なくとも42である。
および基Ar4および基Ar6は、9および10位に結合する。非常に、特に、好ましくは、Ar4および/または基Ar6の少なくとも一つは、1-もしくは2-ナフチル、2-,3-もしくは9-フェナントリルまたは2-,3-,4-,5-,6-もしくは7-ベンズアントラセニルであり、夫々は、6〜50個の炭素原子を有する置換もしくは非置換芳香族炭化水素環状基、5〜50個の非水素原子を有する置換もしくは非置換芳香族ヘテロ環状基、1〜50個の炭素原子を有する置換もしくは非置換アルキル基、3〜50個の核炭素原子を有する置換もしくは非置換シクロアルキル基、1〜50個の炭素原子を含む置換もしくは非置換アルコキシ基、6〜50個の炭素原子を有する置換もしくは非置換アラルキル基、5〜50個の炭素原子を有する置換もしくは非置換アリールオキシ基、5〜50個の炭素原子を有する置換もしくは非置換アリールチオ基、1〜50個の炭素原子を有する置換もしくは非置換アルコキシカルボニル基、1〜50個の炭素原子を有する置換もしくは非置換シリル基、カルボキシ基、ハロゲン原子、シアノ基、ニトロ基またはヒドロキシ基から選ばれる一以上の置換基により置換されてよい。
ここで、kは、1〜8の整数であり、RFはフッ素化アリールもしくはアルキルアリール基または式(COF2O−X+1SHX))のフッ素化アルキルであり、ここで、oは1〜12の整数であり、xは0〜7の整数である。
基R1〜R6は、互いに独立して1〜20個のC原子を有する直鎖もしくは分岐アルキル残基、一以上の非共役二重結合と2〜20個のC原子を夫々有する直鎖もしくは分岐アルケニル残基、一以上の非共役三重結合と2〜20個のC原子を有する直鎖もしくは分岐アルキニル残基および1〜6個のC原子を有するアルキル基でさらに置換することができる3〜7個のC原子を有する飽和、部分飽和もしくは完全飽和のシクロアルキル基、飽和、部分飽和もしくは完全飽和のヘテロアリール基、ヘテロアリールC1−C6アルキル基もしくはアルキルC1−C6アルキル基から選ばれることができ、一以上の置換基Rは、ハロゲン、特に、-Fおよび/または-Clにより部分的にもしくは完全におよび-OR’、-CN、-C(O)OH、-C(O)NR’2、-SO2NR’2、-SO2OH、-SO2X、-NO2により部分的に置換されてよく、ここで、R1〜R6の一もしくは二個の隣接しない非α炭素原子は、-O-、-S-、-S(O)-、-SO2-、-N+R’2-、-C(O)NR’-、-SO2NR’-および-POR-’より成る基から選ばれる単位により置換されてよく、ここで、R’=H、非置換、Fにより部分もしくは完全に置換されたC1〜C6アルキル基、C3〜C7シクロアルキル基、非置換もしくは置換フェニルであり、X=ハロゲンである。
−第1の電極層(アノード)
−随意に、正孔注入層(HIL)、
−随意に、正孔輸送層(HTL)および/または電子障壁層(EBL)、
−電気的もしくは光学的励起により励起子を生じる活性層、
−随意に、電子輸送層(ETL)および/または正孔障壁層(HBL)、
−随意に、電子注入層(EIL)、
−第2の電極層(カソード)
−随意に、第2の基板。
IM2とその前駆体の量子化学計算
有機中性化合物の量子シミュレーションは、Gaussian 03Wソフトウエア(Gaussian Inc.)を使用して実施される。金属を含まない有機化合物のために、まず、半経験法「Ground State/Semi-empirical/ Default spin/AM1」(電荷0/一重項スピン)が、分子ジオメトリーを最適化するために使用され、次いで、エネルギーが、「6-31G(d)」(電荷0/一重項スピン)基本セットをもつTD-DFT法(時間依存濃度関数理論)「TD-SCF/DFT/ Default Spin/B3PW91」により計算される。遷移金属(ランタノイドおよびアクチニドを含む)を含む金属錯体に対しては、ジオメトリー最適化は、「LanL2MB」基本セットをもつHartree-Fockを使用して実施され、エネルギー計算は、次いで、補正関数B3PW91と非金属元素に対する「6-31G(d)」基本セットと遷移金属に対するLanz2DZ (Los Alamos National Laboratory 2-double-z)をもつTD-DFTを使用して実施される。一対のデータをこのような計算により得ることができるが、この分野で量子化学計算により提供される最も重要な結果の一つは、HOMO/LUMOエネルギー準位(最高被占軌道/最低空軌道)、バンドギャップと三重項と一重項励起状態のためのエネルギーである。この結果、第1の励起三重項(T1)と第1の励起一重項(S1)が最も重要である。エネルギー計算からは、ハートリー単位でHOMO HEhおよびLUMO LEhを得る。そして、電子ボルト(eV)でのHOMOおよびLUMO値は、以下の式により決定され、シクロボルタンメトリ(CV)測定を使用する較正から導き出すことができる。
LUMO(eV)=((LEh*27.212)−2.0041)/1.385
これらの値は、本発明において化合物のHOMO−LUMO準位として使用されるだろう。例として、化合物TMM1に対して、−0.21292ハートリーのHOMOと−0.06843ハートリーのLUMOを計算することができ(表1参照。)、較正された−6.05eVのHOMOと較正された−2.79eVのLUMOに夫々対応する。
溶液1および2
本発明のイオン性化合物(IM2)と参照(IM1)とを含む二種の異なる溶液(調合物)が、当分野の当業者に知られた標準的技術を使用して調製された。
2.対応する組成物(表2参照)を23mg/mlの濃度で1:1の重量比のシクロヘキサノンとDMFの混合溶媒中に溶解することによる溶液1および2の調製;
3.グローブボックッス中で溶液を3時間撹拌すること;
4.溶液は、Millipore Millex LS, Hydrophobic PTFE5.0μmを使用して、濾過される。
OLEC1およびOLEC2の調製
アノード/PEDOT/中間層/EML/カソードのサンドイッチ構造において、発光層中でIM1を使用するOLEC1とIM2を使用するOLED2が、次の工程により調製される:
1.PEDOT(Baytron P AI 4083)がITOガラス基板上(Technoprint Inc)に、スピンコーティングにより80nmの厚さで堆積され、次いで、120℃で10分間クリーンルーム内で加熱される;
2.20nmの中間層(IL)が、0.5%濃度を有するHIL-012 (Merck KGaA)のトルエン溶液から、スピンコーティングによりに堆積される、次いで、グローブボックッス中で180℃で10分間加熱される;
3.発光層が、グローブボックッス中で例4によるスピンコーティング溶液により堆積され、160nm厚の層を得る;
4.素子は、50℃で30分間加熱され、次いで、残留溶媒を除去するために、30分間真空室におかれる;
5.Alカソード(150nm)が発光層上の蒸発により堆積される;
6.素子は、UV硬化樹脂、UV樹脂T-470/UR7114 (Nagase Chemtex Corporation)とガラスキャップを使用して封入される。
OLEC1およびOLEC2の特性決定
次いで、OLEC1およびOLEC2が、当業者に知られた標準技術により特性決定される。以下の特性が記録される:VIL特性、ELスペクトルおよび色座標、効率、駆動電圧。
Claims (9)
- Nが、6〜1000g/molの範囲の分子量を有することを特徴とする、請求項1記載の有機発光電子化学電池(OLEC)。
- Mがカチオンであり、Nが、[HSO4]―、[NO3]−、[BF4]−、[(RF)BF3]−、[(RF)2BF2]−、[(RF)3BF]−、[(RF)4B]−、[B(CN)4]−、[H2PO4]−、[(アルキル-O)2PO2]−、[(アルキル)2PO2]−、[(RF)2PO2]−、[RFSO3]−、[HOSO2(CF2)kSO2O]−、[アルキル-SO3]−、[HOSO2(CH2)kSO2O]−、[アルキル-OSO3]−、[アルキル-C(O)O]−、[HO(O)C(CH2)kC(O)O]−、[RFC(O)O]−、[HO(O)C(CF2)kC(O)O]−、[(RFSO2)2N]−、[(FSO2)2N]−、[((RF)2P(O))2N]−、[(RFSO2)3C]−、[(FSO2)3C]− 、PF6 −、[PF3(C2F5)3]−、[PF3(CF3)3]−、[B(COOCOO)2 −、[(CF3SO2)2N]−、[(C2F5SO2)2N]−、[(CF3SO2)(C4F9SO2)N]−、[(CN)2N]−、[CF3SO2]3C]−および[(CN)3C]−を含む基から選ばれることを特徴とし、ここで、kは、1〜8の整数であり、RFはフッ素化アリールもしくはアルキルアリール基または式(COF2O−X+1HX))のフッ素化アルキルであり、ここで、oは1〜12の整数であり、xは0〜7の整数であることを特徴とする、請求項1または2記載の有機発光電子化学電池(OLEC)。
- Mがアニオンであり、Nが、K+、Na+、アンモニウム-、ホスホニウム-、チオウロニウム-、チオキソニウム-、グアニジミウム-カチオン、ヘテロ環カチオンおよびその誘導体を含む基から選ばれることを特徴とする、請求項1または2記載の有機発光電子化学電池(OLEC)。
- マトリックス、蛍光もしくは燐光エミッター、染料、正孔注入材料、正孔輸送材料、電子注入材料および電子輸送材料より成る群から選ばれる機能性有機化合物とを含む請求項1〜4何れか1項記載の有機発光電子化学電池(OLEC)。
- Mの機能性有機基の機能が、機能性有機化合物の機能とは異なることを特徴とする、請求項5記載の有機発光電子化学電池(OLEC)。
- マトリックス化合物および蛍光もしくは燐光エミッター化合物を含む、請求項5または6記載の有機発光電子化学電池(OLEC)。
- イオン伝導性化合物をさらに含む、請求項5〜7何れか1項記載の有機発光電子化学電池(OLEC)。
- マトリックス化合物と染料を含む、請求項5〜8何れか1項記載の有機発光電子化学電池(OLEC)。
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2012
- 2012-02-28 WO PCT/EP2012/000860 patent/WO2012126566A1/en active Application Filing
- 2012-02-28 US US14/007,182 patent/US9923152B2/en not_active Expired - Fee Related
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JP2014511832A (ja) | 2014-05-19 |
US20140014885A1 (en) | 2014-01-16 |
WO2012126566A1 (en) | 2012-09-27 |
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