JP2014527022A - 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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- JP2014527022A JP2014527022A JP2014508701A JP2014508701A JP2014527022A JP 2014527022 A JP2014527022 A JP 2014527022A JP 2014508701 A JP2014508701 A JP 2014508701A JP 2014508701 A JP2014508701 A JP 2014508701A JP 2014527022 A JP2014527022 A JP 2014527022A
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- -1 or from N Inorganic materials 0.000 claims description 36
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- 229920000642 polymer Polymers 0.000 claims description 24
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- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 20
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- 239000000412 dendrimer Substances 0.000 claims description 16
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- 238000005859 coupling reaction Methods 0.000 claims description 13
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- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- YSCWQFAGDUZEQF-UHFFFAOYSA-N bis[3-(3-bromophenyl)phenyl]methanone Chemical compound BrC1=CC=CC(C=2C=C(C=CC=2)C(=O)C=2C=C(C=CC=2)C=2C=C(Br)C=CC=2)=C1 YSCWQFAGDUZEQF-UHFFFAOYSA-N 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
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- KNVVMNKJHCIPRV-UHFFFAOYSA-M lithium;3-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=CC=C2N=C(C([O-])=O)C(O)=CC2=C1 KNVVMNKJHCIPRV-UHFFFAOYSA-M 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
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- SWGQITQOBPXVRC-UHFFFAOYSA-N methyl 2-bromobenzoate Chemical compound COC(=O)C1=CC=CC=C1Br SWGQITQOBPXVRC-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
- 125000004957 naphthylene 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
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- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
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- 230000001590 oxidative effect Effects 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 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
- 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
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 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
- 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
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 125000006850 spacer group Chemical group 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
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 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
- 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
- 229910052721 tungsten Inorganic materials 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
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Abstract
【化1】
Description
A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く、N、OおよびSから選ばれる二個以上のヘテロ原子を有する少なくとも一つの複素環式芳香族五員環を含むか、またはN、OおよびSから選ばれる二個以上のヘテロ原子を有する少なくとも一つの複素環式芳香族六員環を含む5〜20個の芳香族環原子を有するヘテロアリール基、
−1以上の基R1により置換されてよいケト基、または
−1以上の基R1により置換されてよい酸化リン基、または
−1以上の基R1により置換されてよい酸化硫黄基であり、
Yは、BR2、C(R2)2、C=O、Si(R2)2、NR2、O、S、S=OおよびS(=O)2から選ばれる二価基であり;
Xは、出現毎に同一であるか異なり、CR1もしくはNであるか、またはそこに結合する基AをもつCであり;
Zは、出現毎に同一であるか異なり、CR2またはNであり;
Ar1は、1以上の基R1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環構造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、B(OR3)2、CHO、C(=O)R3、CR3=C(R3)2、CN、C(=O)OR3、C(=O)N(R3)2、Si(R3)3、NO2、P(=O)(R3)2、OSO2R3、OR3、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コキシ基、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コキシ基、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6〜30個の芳香族環原子を有する芳香族環構造、または、1以上の基R3で置換されてよい6〜30個の芳香族環原子を有するアリールオキシ基であり;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、B(OR3)2、CHO、C(=O)R3、CR3=C(R3)2、CN、C(=O)OR3、C(=O)N(R3)2、Si(R3)3、N(R3)2、NO2、P(=O)(R3)2、OSO2R3、OR3、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コキシ基、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コキシ基、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、または、1以上の基R3で置換されてよい5〜60個の芳香族環原子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、Cl、Br、I、B(OR4)2、CHO、C(=O)R4、CR4=C(R4)2、CN、C(=O)OR4、C(=O)N(R4)2、Si(R4)3、N(R4)2、NO2、P(=O)(R4)2、OSO2R4、OR4、S(=O)R4、S(=O)2R4、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コキシ基、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コキシ基、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R4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、-R4C=CR4-、-C≡C-、Si(R4)2、C=O、C=S、C=Se、C=NR4、-C(=O)O-、-C(=O)NR4-、NR4、P(=O)(R4)、-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R4により置換されてよい5〜60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、または、1以上の基R4で置換されてよい5〜60個の芳香族環原子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であり;ここで、2個以上の基R3は、たがいに結合してよく、および環を形成してよく;
R4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R4は、たがいに結合してもよく、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または3であり、
ここで、基Zの構成成分としての基R2は、式(I)の環構造上に縮合するいかなる環を形成してはならず;および
さらに、式(II)の基が式(I)中の窒素原子に結合するならば、基Aは、メタもしくはオルト位で芳香族六員環に結合し;
およびさらに、以下の化合物は除外される。
R3は、出現毎に同一であるか異なり、好ましくは、出現毎に同一であるか異なり、H、D、F、CN、Si(R4)3、N(R4)3、1〜10個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜10個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基(上記言及した基は、夫々1以上の基R4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、-C≡C-、-R4C=CR4-、Si(R4)2、C=O、C=NR4、-NR4-、-O-、-S-、-C(=O)O-もしくは-C(=O)NR4-で置き代えられてよい。)または、各場合に、1以上の基R4により置換されてよい5〜20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から選ばれ;ここで、2個以上の基R3は、たがいに結合してよく、および環を形成してよい
好ましい態様では、式(II)の基は、以下の式(II−1)の構造を有する。
Wは、出現毎に同一であるか異なり、CR1またはNであり、および
Vは、NR1、OまたはSであり、および
ここで、少なくとも一つの基Wは、Nである。
基NR2にパラ位で結合する。
(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。
本発明は、さらに、アノード、カソードおよび少なくとも一つの有機層を含む電子素子に関し、ここで、有機層は、少なくとも一つの式(I)の化合物を含む。ここで、電子素子は、好ましくは、上記素子から選ばれ、特に、好ましくは、有機エレクトロルミッセンス素子(OLED)である。
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、無水溶媒中で、保護ガス雰囲気下で行われる。本発明の化合物は、当業者に知られた合成方法により調製することができる。
化合物2−12が同様にして得られる:
化合物14−24が同様にして得られる:
本発明によるOLEDと先行技術にしたがうOLEDが、WO 2004/058911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。
本発明の材料は、特に、燐光OLEDでのマトリックス材料としてか、または単一材料としての(例E1、E2、E8〜E13)または混合マトリックス系での成分としての(例E3〜E7)の使用に適している。非常に良好な性能データを、この場合に達成することができる。たとえば、ドーパントTEG1と組み合わせた化合物H6について、たった3.7Vの電圧、15.5%の外部量子効率および非常に良好なパワー効率48Im/Wが得られる(例E11)。対応するOLEDが定電流密度で駆動されると、初期輝度8000cd/m2が、180h以内で、6400cd/m2に低下するが、これは、良好な値に相当する。
先行技術に従う化合物H1と比べて、20%まで増加した量子効率が、化合物H9とH10の使用について得られる。さらに、顕著な優位性が寿命に関して生じる:約105h以内で、8000cd/m2〜6400cd/m2の輝度の低下が、H1に対する定電流密度での駆動で観察されるが、この値は、H9に対しては約125h後、H10に対しては約140h後に達成されるだけである(例V1、E1およびE2)。H2(先行技術)と比べて、25%をやや超える効率の顕著な改善が、本発明の材料H12で明らかである(例V2、E4)。H12の寿命は約15%より長い。
さらに、本発明の化合物は、電子輸送層で、使用することができる。たとえば、化合物H7と電子注入材料としての厚さ3nmのLiQの層は、3.9Vの電圧と15.3%の量子効率が得られる(例E14)。さらに、この例に対して、非常に良好な寿命が測定される:定電流密度での駆動において、輝度は、約220h以内で、8000cd/m2〜6400cd/m2に低下する。
Claims (15)
- 式(I)の化合物であって、
A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く、N、OおよびSから選ばれる二個以上のヘテロ原子を有する少なくとも一つの複素環式芳香族五員環を含むかまたはN、OおよびSから選ばれる二個以上のヘテロ原子を有する少なくとも一つの複素環式芳香族六員環を含む5〜20個の芳香族環原子を有するヘテロアリール基、
−1以上の基R1により置換されてよいケト基、または
−1以上の基R1により置換されてよい酸化リン基、または
−1以上の基R1により置換されてよい酸化硫黄基であり、
Yは、BR2、C(R2)2、C=O、Si(R2)2、NR2、O、S、S=OおよびS(=O)2から選ばれる二価基であり;
Xは、出現毎に同一であるか異なり、CR1もしくはNであり、またはそこに結合する基AをもつCであり;
Zは、出現毎に同一であるか異なり、CR2またはNであり;
Ar1は、1以上の基R1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環構造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、B(OR3)2、CHO、C(=O)R3、CR3=C(R3)2、CN、C(=O)OR3、C(=O)N(R3)2、Si(R3)3、NO2、P(=O)(R3)2、OSO2R3、OR3、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コキシ基、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コキシ基、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6〜30個の芳香族環原子を有する芳香族環構造、または、1以上の基R3で置換されてよい6〜30個の芳香族環原子を有するアリールオキシ基であり;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、B(OR3)2、CHO、C(=O)R3、CR3=C(R3)2、CN、C(=O)OR3、C(=O)N(R3)2、Si(R3)3、N(R3)2、NO2、P(=O)(R3)2、OSO2R3、OR3、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コキシ基、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コキシ基、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、または、1以上の基R3で置換されてよい5〜60個の芳香族環原子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、Cl、Br、I、B(OR4)2、CHO、C(=O)R4、CR4=C(R4)2、CN、C(=O)OR4、C(=O)N(R4)2、Si(R4)3、N(R4)2、NO2、P(=O)(R4)2、OSO2R4、OR4、S(=O)R4、S(=O)2R4、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コキシ基、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コキシ基、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R4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、-R4C=CR4-、-C≡C-、Si(R4)2、C=O、C=S、C=Se、C=NR4、-C(=O)O-、-C(=O)NR4-、NR4、P(=O)(R4)、-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R4により置換されてよい5〜60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、または、1以上の基R4で置換されてよい5〜60個の芳香族環原子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であり;ここで、2個以上の基R3は、たがいに結合してよく、および環を形成してよく;
R4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R4は、たがいに結合してもよく、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または3であり、
ここで、基Zの構成成分としての基R2は、式(I)の環構造上に縮合するいかなる環を形成してはならず;および
さらに、式(II)の基が式(I)中の窒素原子に結合するならば、基Aは、メタもしくはオルト位で芳香族六員環に結合し;
およびさらに、以下の化合物は除外される。
- 式(I)に示されるアミノ基に加えて、さらなる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。
- 基Ar1は、各々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環構造または5〜18個の芳香族環原子を有する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または2記載の化合物。
- 基Yは、C(R2)2、Si(R2)2、NR2、OおよびSから選ばれ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。
- 式(II)の基毎の一個を超えない基X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。
- 芳香族六員環毎の一個を超えない基Zは、Nであることを特徴とする、請求項1〜5何れか1項記載の電子素子:
- R1は、出現毎に同一であるか異なり、H、D、F、CN、Si(R3)3、1〜10個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜10個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基、(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、-C≡C-、-R3C=CR3-、Si(R3)2、C=O、C=NR3、NR3、-O-、-S-、-C(=O)O-もしくは-C(=O)NR3-で置き代えられてよい。)または、1以上の基R3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環構造から選ばれ;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いことを特徴とする、請求項1〜6何れか1項記載の化合物;
- 基Aに結合しない基R1は、H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。
- ポリマー、オリゴマーもしくはデンドリマーへの結合が、式(I)中でR1、R2またはR3により置換される任意の所望の位置に局在化されてよい、請求項1〜10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。
- 少なくとも一つの請求項1〜10何れか1項記載の化合物または少なくとも一つの請求項11記載のポリマー、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記載の式(II)の構造を含む少なくとも一つの基が、金属触媒カップリング反応で導入されることを特徴とする請求項1〜10何れか1項記載の化合物の製造方法。
- 好ましくは、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、少なくとも一つの請求項1〜10何れか1項記載の化合物または少なくとも一つの請求項11記載のポリマー、オリゴマーもしくはデンドリマーを含む電子素子。
- 請求項1〜10何れか1項記載の化合物または請求項11記載のポリマー、オリゴマーもしくはデンドリマーが、発光層中でのマトリックス材料としておよび/または電子輸送層もしくは電子注入層中で電子輸送材料としておよび/または正孔障壁層中で正孔障壁材料として存在することを特徴とする、請求項14記載の有機エレクトロルミッセンス素子。
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016158540A1 (ja) * | 2015-03-27 | 2016-10-06 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子、電子機器、および化合物 |
WO2017115753A1 (ja) * | 2015-12-28 | 2017-07-06 | コニカミノルタ株式会社 | 架橋化合物、有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP2017137284A (ja) * | 2016-01-29 | 2017-08-10 | 国立大学法人山形大学 | ターピリジン誘導体、それよりなる発光材料及びそれを用いた有機el素子 |
JP2021001175A (ja) * | 2016-05-26 | 2021-01-07 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 含窒素化合物及び含窒素化合物を含む有機電界発光素子 |
Families Citing this family (47)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2020046049A1 (ko) | 2018-08-31 | 2020-03-05 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
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KR20200087906A (ko) | 2019-01-11 | 2020-07-22 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 |
KR20200094262A (ko) | 2019-01-29 | 2020-08-07 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 |
CN110615759B (zh) * | 2019-09-25 | 2020-08-11 | 陕西莱特光电材料股份有限公司 | 化合物、光电转化器件及电子装置 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03190870A (ja) * | 1989-11-29 | 1991-08-20 | Ciba Geigy Ag | 光互変性化合物、それらの製造法及び用途 |
JPH11199565A (ja) * | 1997-10-17 | 1999-07-27 | Toyama Chem Co Ltd | 含窒素三・四環式化合物およびそれを含有する抗ウイルス剤 |
JP2007070620A (ja) * | 2005-08-12 | 2007-03-22 | Sumitomo Chemical Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
JP2008522389A (ja) * | 2004-11-25 | 2008-06-26 | ビーエーエスエフ ソシエタス・ヨーロピア | 有機発光ダイオード用のマトリクス材料としてのフェノチアジン−s−オキシド及びフェノチアジン−s,s−ジオキシドの使用 |
JP2010013444A (ja) * | 2008-06-25 | 2010-01-21 | Gracel Display Inc | 新規な有機電界発光化合物及びこれを使用する有機電界発光素子 |
JP2010045301A (ja) * | 2008-08-18 | 2010-02-25 | Fuji Xerox Co Ltd | 有機電界発光素子、及びその表示媒体 |
JP2010128458A (ja) * | 2008-12-01 | 2010-06-10 | Fuji Xerox Co Ltd | 画像形成装置用像保持体、プロセスカートリッジ及び画像形成装置 |
WO2010147319A2 (ko) * | 2009-06-19 | 2010-12-23 | 주식회사 두산 | 아크리딘 유도체 및 이를 포함하는 유기 전계 발광 소자 |
JP2011026376A (ja) * | 2009-07-21 | 2011-02-10 | Fujifilm Corp | 色素、これを用いた光電変換素子及び光電気化学電池 |
JP2011210749A (ja) * | 2010-03-26 | 2011-10-20 | Fujifilm Corp | 有機電界発光素子及び電荷輸送材料 |
Family Cites Families (95)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
DE4111878A1 (de) | 1991-04-11 | 1992-10-15 | Wacker Chemie Gmbh | Leiterpolymere mit konjugierten doppelbindungen |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
JPH07133483A (ja) | 1993-11-09 | 1995-05-23 | Shinko Electric Ind Co Ltd | El素子用有機発光材料及びel素子 |
EP0676461B1 (de) | 1994-04-07 | 2002-08-14 | Covion Organic Semiconductors GmbH | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
DE4436773A1 (de) | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
WO1997005184A1 (en) | 1995-07-28 | 1997-02-13 | The Dow Chemical Company | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
DE19614971A1 (de) | 1996-04-17 | 1997-10-23 | Hoechst Ag | Polymere mit Spiroatomen und ihre Verwendung als Elektrolumineszenzmaterialien |
DE19652261A1 (de) | 1996-12-16 | 1998-06-18 | Hoechst Ag | Arylsubstituierte Poly(p-arylenvinylene), Verfahren zur Herstellung und deren Verwendung in Elektroluminszenzbauelementen |
DE19846766A1 (de) | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere, enthaltend spezielle Fluorenbausteine mit verbesserten Eigenschaften |
US6166172A (en) | 1999-02-10 | 2000-12-26 | Carnegie Mellon University | Method of forming poly-(3-substituted) thiophenes |
DE60031729T2 (de) | 1999-05-13 | 2007-09-06 | The Trustees Of Princeton University | Lichtemittierende, organische, auf elektrophosphoreszenz basierende anordnung mit sehr hoher quantenausbeute |
KR100794975B1 (ko) | 1999-12-01 | 2008-01-16 | 더 트러스티즈 오브 프린스턴 유니버시티 | 유기 led용 인광성 도펀트로서 l2mx 형태의 착물 |
TW532048B (en) | 2000-03-27 | 2003-05-11 | Idemitsu Kosan Co | Organic electroluminescence element |
US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
CN100505375C (zh) | 2000-08-11 | 2009-06-24 | 普林斯顿大学理事会 | 有机金属化合物和发射转换有机电致磷光 |
JP4344494B2 (ja) * | 2000-08-24 | 2009-10-14 | 富士フイルム株式会社 | 発光素子及び新規重合体子 |
JP4154140B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物 |
JP4154138B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子、表示装置及び金属配位化合物 |
JP4154139B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子 |
GB0104177D0 (en) | 2001-02-20 | 2001-04-11 | Isis Innovation | Aryl-aryl dendrimers |
WO2002072714A1 (de) | 2001-03-10 | 2002-09-19 | Covion Organic Semiconductors Gmbh | Lösung und dispersionen organischer halbleiter |
DE10141624A1 (de) | 2001-08-24 | 2003-03-06 | Covion Organic Semiconductors | Lösungen polymerer Halbleiter |
DE10159946A1 (de) | 2001-12-06 | 2003-06-18 | Covion Organic Semiconductors | Prozess zur Herstellung von Aryl-Aryl gekoppelten Verbindungen |
ITRM20020411A1 (it) | 2002-08-01 | 2004-02-02 | Univ Roma La Sapienza | Derivati dello spirobifluorene, loro preparazione e loro uso. |
DE10249723A1 (de) | 2002-10-25 | 2004-05-06 | Covion Organic Semiconductors Gmbh | Arylamin-Einheiten enthaltende konjugierte Polymere, deren Darstellung und Verwendung |
GB0226010D0 (en) | 2002-11-08 | 2002-12-18 | Cambridge Display Tech Ltd | Polymers for use in organic electroluminescent devices |
JP4287198B2 (ja) | 2002-11-18 | 2009-07-01 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
US20060063027A1 (en) | 2002-12-23 | 2006-03-23 | Covion Organic Semiconductors Gmbh | Organic electroluminescent element |
DE10304819A1 (de) | 2003-02-06 | 2004-08-19 | Covion Organic Semiconductors Gmbh | Carbazol-enthaltende konjugierte Polymere und Blends, deren Darstellung und Verwendung |
JP4411851B2 (ja) | 2003-03-19 | 2010-02-10 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
CN1768029B (zh) | 2003-04-10 | 2012-02-08 | 出光兴产株式会社 | 芳香族胺衍生物和采用该衍生物的有机场致发光元件 |
KR101162933B1 (ko) | 2003-04-15 | 2012-07-05 | 메르크 파텐트 게엠베하 | 매트릭스 재료 및 방출 가능 유기 반도체의 혼합물, 그의 용도 및 상기 혼합물을 함유하는 전자 부품 |
EP1617710B1 (en) | 2003-04-23 | 2015-05-20 | Konica Minolta Holdings, Inc. | Material for organic electroluminescent device, organic electroluminescent device, illuminating device and display |
EP1491568A1 (en) | 2003-06-23 | 2004-12-29 | Covion Organic Semiconductors GmbH | Semiconductive Polymers |
DE10328627A1 (de) | 2003-06-26 | 2005-02-17 | Covion Organic Semiconductors Gmbh | Neue Materialien für die Elektrolumineszenz |
EP1644459B1 (de) | 2003-07-07 | 2017-08-23 | Merck Patent GmbH | Mischungen von organischen zur emission befähigten halbleitern und matrixmaterialien,sowie elektronikbauteile diese enthaltend |
DE10333232A1 (de) | 2003-07-21 | 2007-10-11 | Merck Patent Gmbh | Organisches Elektrolumineszenzelement |
DE10337346A1 (de) | 2003-08-12 | 2005-03-31 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere enthaltend Dihydrophenanthren-Einheiten und deren Verwendung |
DE10338550A1 (de) | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
KR20110112474A (ko) | 2003-09-12 | 2011-10-12 | 스미또모 가가꾸 가부시키가이샤 | 덴드리머 화합물 및 그것을 사용한 유기 발광 소자 |
DE10345572A1 (de) | 2003-09-29 | 2005-05-19 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
US7795801B2 (en) | 2003-09-30 | 2010-09-14 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, illuminator, display and compound |
EP2366752B1 (de) | 2003-10-22 | 2016-07-20 | Merck Patent GmbH | Neue materialien für die elektrolumineszenz und deren verwendung |
US20070190355A1 (en) | 2004-03-08 | 2007-08-16 | Idemitsu Kosan Co., Ltd | Material for organic electroluminescence device and organic electroluminescence device utilizing the same |
US7790890B2 (en) | 2004-03-31 | 2010-09-07 | Konica Minolta Holdings, Inc. | Organic electroluminescence element material, organic electroluminescence element, display device and illumination device |
DE102004020298A1 (de) | 2004-04-26 | 2005-11-10 | Covion Organic Semiconductors Gmbh | Elektrolumineszierende Polymere und deren Verwendung |
DE102004023277A1 (de) | 2004-05-11 | 2005-12-01 | Covion Organic Semiconductors Gmbh | Neue Materialmischungen für die Elektrolumineszenz |
US7598388B2 (en) | 2004-05-18 | 2009-10-06 | The University Of Southern California | Carbene containing metal complexes as OLEDs |
TWI327563B (en) | 2004-05-24 | 2010-07-21 | Au Optronics Corp | Anthracene compound and organic electroluminescent device including the anthracene compound |
JP4862248B2 (ja) | 2004-06-04 | 2012-01-25 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
JP2006001973A (ja) | 2004-06-15 | 2006-01-05 | Fujitsu Ltd | ポリ乳酸樹脂組成物、並びに、成型体及びその製造方法、及びoa機器 |
DE102004031000A1 (de) | 2004-06-26 | 2006-01-12 | Covion Organic Semiconductors Gmbh | Organische Elektrolumineszenzvorrichtungen |
TW200613515A (en) | 2004-06-26 | 2006-05-01 | Merck Patent Gmbh | Compounds for organic electronic devices |
DE102004032527A1 (de) | 2004-07-06 | 2006-02-02 | Covion Organic Semiconductors Gmbh | Elektrolumineszierende Polymere |
ITRM20040352A1 (it) | 2004-07-15 | 2004-10-15 | Univ Roma La Sapienza | Derivati oligomerici dello spirobifluorene, loro preparazione e loro uso. |
JP4782130B2 (ja) | 2004-09-24 | 2011-09-28 | エルジー・ケム・リミテッド | 新しい有機発光素子材料およびこれを用いた有機発光素子(7) |
TW200639140A (en) | 2004-12-01 | 2006-11-16 | Merck Patent Gmbh | Compounds for organic electronic devices |
EP1669386A1 (de) | 2004-12-06 | 2006-06-14 | Covion Organic Semiconductors GmbH | Teilkonjugierte Polymere, deren Darstellung und Verwendung |
CN101087776B (zh) | 2004-12-24 | 2012-07-04 | 先锋公司 | 有机化合物、电荷传输材料和有机电致发光元件 |
JP4263700B2 (ja) | 2005-03-15 | 2009-05-13 | 出光興産株式会社 | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
CN101171320B (zh) | 2005-05-03 | 2013-04-10 | 默克专利有限公司 | 有机电致发光器件 |
DE102005023437A1 (de) | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
EP1901615A2 (en) | 2005-07-08 | 2008-03-26 | Unilever N.V. | Food product and process for preparing it |
DE102005037734B4 (de) | 2005-08-10 | 2018-02-08 | Merck Patent Gmbh | Elektrolumineszierende Polymere, ihre Verwendung und bifunktionelle monomere Verbindungen |
KR101082258B1 (ko) | 2005-12-01 | 2011-11-09 | 신닛테츠가가쿠 가부시키가이샤 | 유기 전계 발광소자용 화합물 및 유기 전계 발광소자 |
DE102005058543A1 (de) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
DE102005058557A1 (de) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102005060473A1 (de) | 2005-12-17 | 2007-06-28 | Merck Patent Gmbh | Konjugierte Polymere, deren Darstellung und Verwendung |
KR101243918B1 (ko) * | 2006-01-03 | 2013-03-14 | 삼성디스플레이 주식회사 | 청색 발광 고분자, 그 제조방법 및 이를 채용한 유기 전계발광 소자 |
DE102006015183A1 (de) | 2006-04-01 | 2007-10-04 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006025777A1 (de) | 2006-05-31 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006025846A1 (de) | 2006-06-02 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006031990A1 (de) | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
WO2008056746A1 (fr) | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique |
DE102007002714A1 (de) | 2007-01-18 | 2008-07-31 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
WO2008123189A1 (ja) | 2007-03-26 | 2008-10-16 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子用化合物及び有機電界発光素子 |
DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
JP5609024B2 (ja) * | 2008-06-30 | 2014-10-22 | 住友化学株式会社 | フェノキサジン系高分子化合物及びそれを用いた発光素子 |
DE102008033943A1 (de) | 2008-07-18 | 2010-01-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008035413A1 (de) | 2008-07-29 | 2010-02-04 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
DE102008036982A1 (de) | 2008-08-08 | 2010-02-11 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
JP5701766B2 (ja) | 2008-11-11 | 2015-04-15 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネセント素子 |
DE102008056688A1 (de) | 2008-11-11 | 2010-05-12 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
KR101594129B1 (ko) * | 2008-11-28 | 2016-02-16 | 삼성전자주식회사 | 발광 고분자 및 상기 발광 고분자를 포함한 유기 발광 소자 |
JP5551428B2 (ja) * | 2009-01-06 | 2014-07-16 | ユー・ディー・シー アイルランド リミテッド | 電荷輸送材料及び有機電界発光素子 |
DE102009005290A1 (de) | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
DE102009014513A1 (de) | 2009-03-23 | 2010-09-30 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102009023155A1 (de) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009031021A1 (de) | 2009-06-30 | 2011-01-05 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010005697A1 (de) | 2010-01-25 | 2011-07-28 | Merck Patent GmbH, 64293 | Verbindungen für elektronische Vorrichtungen |
KR101792175B1 (ko) * | 2010-04-05 | 2017-11-01 | 에스에프씨 주식회사 | 스피로 화합물 및 이를 포함하는 유기전계발광소자 |
KR101759482B1 (ko) * | 2010-04-09 | 2017-07-20 | 에스에프씨 주식회사 | 이형고리 화합물 및 이를 포함하는 유기전계발광소자 |
DE102010014933A1 (de) | 2010-04-14 | 2011-10-20 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
JP5850835B2 (ja) | 2010-06-07 | 2016-02-03 | 保土谷化学工業株式会社 | アクリダン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
-
2012
- 2012-04-12 CN CN201280021987.4A patent/CN103503188B/zh active Active
- 2012-04-12 JP JP2014508701A patent/JP6195823B2/ja not_active Expired - Fee Related
- 2012-04-12 WO PCT/EP2012/001600 patent/WO2012149999A1/de active Application Filing
- 2012-04-12 US US14/115,107 patent/US10177312B2/en not_active Expired - Fee Related
- 2012-04-12 EP EP12714970.6A patent/EP2705550B1/de active Active
- 2012-04-12 KR KR1020137032153A patent/KR102014552B1/ko active IP Right Grant
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03190870A (ja) * | 1989-11-29 | 1991-08-20 | Ciba Geigy Ag | 光互変性化合物、それらの製造法及び用途 |
JPH11199565A (ja) * | 1997-10-17 | 1999-07-27 | Toyama Chem Co Ltd | 含窒素三・四環式化合物およびそれを含有する抗ウイルス剤 |
JP2008522389A (ja) * | 2004-11-25 | 2008-06-26 | ビーエーエスエフ ソシエタス・ヨーロピア | 有機発光ダイオード用のマトリクス材料としてのフェノチアジン−s−オキシド及びフェノチアジン−s,s−ジオキシドの使用 |
JP2007070620A (ja) * | 2005-08-12 | 2007-03-22 | Sumitomo Chemical Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
JP2010013444A (ja) * | 2008-06-25 | 2010-01-21 | Gracel Display Inc | 新規な有機電界発光化合物及びこれを使用する有機電界発光素子 |
JP2010045301A (ja) * | 2008-08-18 | 2010-02-25 | Fuji Xerox Co Ltd | 有機電界発光素子、及びその表示媒体 |
JP2010128458A (ja) * | 2008-12-01 | 2010-06-10 | Fuji Xerox Co Ltd | 画像形成装置用像保持体、プロセスカートリッジ及び画像形成装置 |
WO2010147319A2 (ko) * | 2009-06-19 | 2010-12-23 | 주식회사 두산 | 아크리딘 유도체 및 이를 포함하는 유기 전계 발광 소자 |
JP2011026376A (ja) * | 2009-07-21 | 2011-02-10 | Fujifilm Corp | 色素、これを用いた光電変換素子及び光電気化学電池 |
JP2011210749A (ja) * | 2010-03-26 | 2011-10-20 | Fujifilm Corp | 有機電界発光素子及び電荷輸送材料 |
Non-Patent Citations (6)
Title |
---|
CHOI, J. ET AL., SYNTHETIC METALS, vol. 159, JPN6017003636, 2009, pages 1922 - 7, ISSN: 0003494221 * |
HAUCK, MARTINA; TURDEAN, RALUCA; MEMMINGER, KARIN; SCHOENHABER, JAN; ROMINGER, FRANK; MUELLER, T. J.: "Luminescent, Redox-Active Diphenothiazine Dumbbells Expanded by Conjugated Arenes and Heteroarenes", JOURNAL OF ORGANIC CHEMISTRY, vol. 75(24), JPN6015053033, 2010, pages 8591 - 8603, ISSN: 0003229286 * |
HELLWINKEL, DIETER; SCHMIDT, WERNER: "Modified tetrahelicene systems. III. Doubly ortho-bridged triphenylamine derivatives", CHEMISCHE BERICHTE, vol. 113(1), JPN7015003664, 1980, pages 358 - 84, ISSN: 0003229288 * |
NARULE M. ET AL., E-JOURNAL OF CHEMISTRY, vol. 4, no. 1, JPN6017003637, 2007, pages 53 - 9, ISSN: 0003598993 * |
SAILER, MARKUS; GROPEANU, RADU-ADRIAN; MUELLER, THOMAS J. J.: "Practical Synthesis of Iodo Phenothiazines. A Facile Access to Electrophore Building Blocks", JOURNAL OF ORGANIC CHEMISTRY, vol. 68(19), JPN6015053034, 2003, pages 7509 - 7512, ISSN: 0003229287 * |
SAWHNEY, S. N. ET AL., J. INDIAN CHEM. SOC., vol. Vol. LXV, JPN6017026139, 1988, pages 643 - 7, ISSN: 0003598997 * |
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JP2021001175A (ja) * | 2016-05-26 | 2021-01-07 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 含窒素化合物及び含窒素化合物を含む有機電界発光素子 |
JP7078961B2 (ja) | 2016-05-26 | 2022-06-01 | 三星ディスプレイ株式會社 | 含窒素化合物及び含窒素化合物を含む有機電界発光素子 |
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US20140070146A1 (en) | 2014-03-13 |
JP6195823B2 (ja) | 2017-09-13 |
WO2012149999A1 (de) | 2012-11-08 |
KR20140045368A (ko) | 2014-04-16 |
EP2705550B1 (de) | 2017-07-05 |
EP2705550A1 (de) | 2014-03-12 |
CN103503188A (zh) | 2014-01-08 |
US10177312B2 (en) | 2019-01-08 |
KR102014552B1 (ko) | 2019-10-21 |
CN103503188B (zh) | 2016-08-31 |
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