JP2015502960A - 電子素子のための化合物 - Google Patents
電子素子のための化合物 Download PDFInfo
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- JP2015502960A JP2015502960A JP2014546340A JP2014546340A JP2015502960A JP 2015502960 A JP2015502960 A JP 2015502960A JP 2014546340 A JP2014546340 A JP 2014546340A JP 2014546340 A JP2014546340 A JP 2014546340A JP 2015502960 A JP2015502960 A JP 2015502960A
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 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
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical class C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing 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
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003751 zinc Chemical class 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
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Abstract
Description
Wは、CHまたはNであり;
Ar1は、出現毎に同一であるか異なり、1以上の基R1により置換されてよい6〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
Ar2は、出現毎に同一であるか異なり、1以上の基R1により置換されてよい6〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、C(=O)R2、CN、Si(R2)3、NO2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、1〜20個のC原子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、3〜20個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基、2〜20個のC原子を有するアルケニルもしくはアルキニル基(上記言及した基は、夫々1以上の基R2により置換されてよく、上記言及した基中の1以上のCH2基は、-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、-C(=O)NR2-、NR2、P(=O)(R2)、-O-、-S-、SOもしくはSO2で置き代えられてよく、ここで、上記言及した基中の1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;ここで、2個以上の基R1は、たがいに結合してよく、および環を形成してよく;
R2は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、C(=O)R3、CN、Si(R3)3、NO2、P(=O)(R3)2、S(=O)R3、S(=O)2R3、1〜20個のC原子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、3〜20個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基、2〜20個のC原子を有するアルケニルもしくはアルキニル基(上記言及した基は、夫々1以上の基R3により置換されてよく、上記言及した基中の1以上のCH2基は、-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=S、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SOもしくはSO2で置き代えられてよく、ここで、上記言及した基中の1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R3により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;ここで、2個以上の基R2は、たがいに結合してよく、および環を形成してよく;
R3は、出現毎に同一であるか異なり、H、D、F、1〜20個のC原子を有する脂肪族、芳香族もしくは複素環式芳香族有機基であって、さらに、1以上のH原子は、DもしくはFで置き代えられてよく;ここで、2個以上の置換基R3は、たがいに結合してよく、および環を形成してよく;
nは、出現毎に同一であるか異なり、0、1、2、3、4または5であり;
mは、0、1、2または3であり;
ここで、中央の窒素原子に結合する三個の基は、全体として、全て同一ではなく、および
以下の化合物は、除外される。
aおよびbは、互いに、同一か異なり、0または1であってよく、および
基は、破線を介して式(I)の親構造に結合するか、または
式(Ar1-2)の基である。
cおよびdは、互いに、同一か異なり、0または1であってよく、および
基は、破線を介して式(I)の親構造に結合する
基Ar1の、非常に、特に、好ましい態様は、以下の式(Ar1-a)〜(Ar1-d)である。
基は、破線を介して式(I)の親構造に結合する。
eは、各場合に、同一か異なり、0または1であってよく、および
基は、破線を介して式(I)の親構造に結合する。
(A)スズキ重合;
(B)ヤマモト重合;
(C)スチル重合および
(D)ハートウイッグ-ブッフバルト重合
重合をこれらの方法により実行することができる方法と次いでポリマーを反応媒体から分離し、精製することができる方法は、当業者に知られており、文献、たとえば、WO 2003/048225、WO 2004/037887およびWO 2004/037887に詳細に記載されている。
本発明の有機エレクトロルミネセンス素子の正孔注入もしくは正孔輸送層中で、または電子輸送層中で使用することができる適切な電荷輸送材料は、たとえば、Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010に開示された化合物または先行技術によりこれらの層に使用される他の材料である。
A)合成例
以下の合成は、他に断らない限り、保護ガス雰囲気下、無水溶媒中で行われる。出発物質は、たとえば、アルドリッチ(ALDRICH)またはABCRから購入することができる。括弧内の番号は、CAS番号に関する。
本発明によるOLEDと先行技術にしたがうOLEDが、WO 04/058911にしたがう一般的プロセスにより製造されるが、ここに記載される状況(層の厚さの変化、材料)に適合される。
厚さ150nmの構造化されたITO(インジウム錫酸化物)で被覆されたガラス板が、改善された加工のために、20nmのPEDOT(ポリ(3,4-エチレンジオキシ-2,5-チオフェン)ポリ(スチレンスホネート、水からのスピンコートにより適用、H. C. Starck, Goslar,独から購入。)で被覆される。これらの被覆されたガラス板は、OLEDが適用される基板を形成する。OLEDは、基本的に、次の層構造を有する:基板/正孔注入層(HIL)/正孔輸送層(HTL)/中間層(IL)/随意に正孔輸送層(HTL2)、電子ブロック層(EBL)/発光層(EML)/電子輸送層(ETL)および最後にカソード。カソードは、100nm厚のアルミニウム層により形成される。OLEDの正確な構造は、表1と2に示される。OLEDの製造のために必要とされる材料は、表5に示される。
Claims (16)
- 以下が、出現する記号と添え字に適用される式(I)の化合物;
Wは、CHまたはNであり;
Ar1は、出現毎に同一であるか異なり、1以上の基R1により置換されてよい6〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
Ar2は、出現毎に同一であるか異なり、1以上の基R1により置換されてよい6〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、C(=O)R2、CN、Si(R2)3、NO2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、1〜20個のC原子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、3〜20個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基、2〜20個のC原子を有するアルケニルもしくはアルキニル基(上記言及した基は、夫々1以上の基R2により置換されてよく、上記言及した基中の1以上のCH2基は、-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、-C(=O)NR2-、NR2、P(=O)(R2)、-O-、-S-、SOもしくはSO2で置き代えられてよく、ここで、上記言及した基中の1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;ここで、2個以上の基R1は、たがいに結合してよく、および環を形成してよく;
R2は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、C(=O)R3、CN、Si(R3)3、NO2、P(=O)(R3)2、S(=O)R3、S(=O)2R3、1〜20個のC原子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、3〜20個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基、2〜20個のC原子を有するアルケニルもしくはアルキニル基(上記言及した基は、夫々1以上の基R3により置換されてよく、上記言及した基中の1以上のCH2基は、-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=S、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SOもしくはSO2で置き代えられてよく、ここで、上記言及した基中の1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R3により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;ここで、2個以上の基R2は、たがいに結合してよく、および環を形成してよく;
R3は、出現毎に同一であるか異なり、H、D、F、1〜20個のC原子を有する脂肪族、芳香族もしくは複素環式芳香族有機基であって、さらに、1以上のH原子は、DもしくはFで置き代えられてよく;ここで、2個以上の置換基R3は、たがいに結合してよく、および環を形成してよく;
nは、出現毎に同一であるか異なり、0、1、2、3、4または5であり;
mは、0、1、2または3であり;
ここで、中央の窒素原子に結合する三個の基は、全体として、全て同一ではなく、および
以下の化合物は、除外される。
- 式(I)中に示されるトリアリールアミノ基とは別のさらなるアリールアミノ基を含まないことを特徴とする、請求項1記載の化合物。
- ヘテロアリール基と複素環式芳香族環構造を含まないことを特徴とする、請求項1または2記載の化合物。
- Wは、CHであることを特徴とする、請求項1〜3何れか1項記載の化合物。
- 環中の0、1、2または3個の基Zは、Nであり、ここで、二個を超えない隣接する基Zは、Nであることを特徴とする、請求項1〜4何れか1項記載の化合物。
- Ar1は、出現毎に同一であるか異なり、1以上の基R1により置換されてよい6〜18個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であることを特徴とする、請求項1〜5何れか1項記載の化合物。
- 式(I)の化合物中の少なくとも一つの基Ar1は、中央の窒素原子へ結合に対して、メタ位で六員環に結合することを特徴とする、請求項1〜6何れか1項記載の化合物。
- Ar2は、出現毎に同一であるか異なり、1以上の基R1により置換されてよい6〜12個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であることを特徴とする、請求項1〜7何れか1項記載の化合物。
- nは、1または2であることを特徴とする、請求項1〜8何れか1項記載の化合物。
- mは、0または1、好ましくは、0であることを特徴とする、請求項1〜9何れか1項記載の化合物。
- Ar1は、中央の窒素原子へ結合に対して、オルト位で六員環に結合しないことを特徴とする、請求項1〜10何れか1項記載の化合物。
- アミノ基を含むアリール化合物と、脱離基を含むアリール化合物が、遷移金属触媒カップリング反応で互いに結合することを特徴とする、請求項1〜11何れか1項記載の化合物の製造方法。
- オリゴマー、ポリマーもしくはデンドリマーへの結合が、式(I)中でR1により置換された任意の所望の位置に位置してよい、請求項1〜11何れか1項記載の一以上の化合物を含む、オリゴマー、ポリマーまたはデンドリマー。
- 請求項1〜11何れか1項記載の少なくとも一つの化合物または請求項13記載の少なくとも一つのポリマー、オリゴマーもしくはデンドリマーと少なくとも一つの溶媒を含む調合物。
- 請求項1〜11何れか1項記載の少なくとも一つの化合物または請求項13記載の少なくとも一つのポリマー、オリゴマーもしくはデンドリマーを含むことを特徴とする有機集積回路(O-IC)、有機電界効果トランジスタ(O-FET)、有機薄膜トランジスタ(O-TFT)、有機発光トランジスタ(O-LET)、有機太陽電池(O-SC)、有機光学検査器、有機光受容器、有機電場消光素子(O-FQD)、発光電子化学電池(LEC)、有機レーザーダイオード(O-laser)および有機エレクトロルミネッセンス素子(OLED)から選ばれる電子素子。
- 有機エレクトロルミッセンス素子から選ばれ、請求項1〜11何れか1項記載の化合物が、一以上の以下の層で使用されることを特徴とする、請求項15記載の電子素子;
-正孔輸送層、正孔注入層中もしくは電子ブロック層中で正孔輸送材料として、
-一以上の蛍光もしくは燐光ドーパントと組み合わせて発光層中でのマトリックス材料として。
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Also Published As
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US10424739B2 (en) | 2019-09-24 |
WO2013087142A1 (de) | 2013-06-20 |
US20140312287A1 (en) | 2014-10-23 |
JP2018035169A (ja) | 2018-03-08 |
US20180269398A1 (en) | 2018-09-20 |
KR20140103146A (ko) | 2014-08-25 |
KR101961613B1 (ko) | 2019-03-25 |
JP6570834B2 (ja) | 2019-09-04 |
CN103998415A (zh) | 2014-08-20 |
KR20180126629A (ko) | 2018-11-27 |
KR101921896B1 (ko) | 2018-11-26 |
KR20170083154A (ko) | 2017-07-17 |
CN105742499B (zh) | 2018-02-13 |
US10665787B2 (en) | 2020-05-26 |
CN105742499A (zh) | 2016-07-06 |
US20180269399A1 (en) | 2018-09-20 |
CN103998415B (zh) | 2016-10-12 |
EP2791105A1 (de) | 2014-10-22 |
EP2791105B1 (de) | 2020-03-18 |
US10008672B2 (en) | 2018-06-26 |
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