JP6230916B2 - 置換ジベンゾナフタセン - Google Patents
置換ジベンゾナフタセン Download PDFInfo
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- JP6230916B2 JP6230916B2 JP2013552869A JP2013552869A JP6230916B2 JP 6230916 B2 JP6230916 B2 JP 6230916B2 JP 2013552869 A JP2013552869 A JP 2013552869A JP 2013552869 A JP2013552869 A JP 2013552869A JP 6230916 B2 JP6230916 B2 JP 6230916B2
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- 230000004888 barrier function Effects 0.000 claims description 22
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- 238000002360 preparation method Methods 0.000 claims description 14
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 12
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- 238000001126 phototherapy Methods 0.000 claims description 10
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
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- 238000005401 electroluminescence Methods 0.000 claims description 6
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 8
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 7
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 7
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- 150000004982 aromatic amines Chemical class 0.000 description 7
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- 239000012074 organic phase Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 7
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
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- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 6
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- 229910052751 metal Inorganic materials 0.000 description 6
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- 230000002265 prevention Effects 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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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
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- 125000002102 aryl alkyloxo group Chemical group 0.000 description 5
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- 125000005553 heteroaryloxy group Chemical group 0.000 description 5
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 5
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- 125000005055 alkyl alkoxy group Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
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Description
T、U、V、Wは、出現毎に同一であるか異なり、CR1、N、PまたはPR1 2であり;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、N(R2)2、CN、NO2、Si(R2)3、B(OR2)2、C(=O)R2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、OSO2R2、1〜40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、2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルケニル、アルキニル、アルコキシ、アルキルアルコキシもしくはチオアルコキシ基(夫々は、1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R3)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き代えられてよく、ここで、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5〜60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R2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、アリールアルコキシもしくはヘテロアリールオキシ基、または1以上の基R2により置換されてよい10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基または二個以上のこれら基の組み合わせまたは架橋可能基Qであり;
R2は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、N(R3)2、CN、NO2、Si(R3)3、B(OR3)2、C(=O)R3、P(=O)(R3)2、S(=O)R3、S(=O)2R3、OSO2R3、1〜40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、2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルケニル、アルキニル、アルコキシ、アルキルアルコキシもしくはチオアルコキシ基(夫々は、1以上の基R3により置換されてよく、1以上の隣接しないCH2基は、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、NR3、O、SもしくはCONR3で置き代えられてよく、ここで、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5〜60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、アリールアルコキシもしくはヘテロアリールオキシ基、または1以上の基R3により置換されてよい10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基または二個以上のこれら基の組み合わせであり;ここで、2個以上の隣接する置換基R2は、モノあるいはポリ環式の脂肪族もしくは芳香族環構造を互いに形成してもよく;
R3は、出現毎に同一であるか異なり、H、D、Fまたは1〜40個のC原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素基(さらに、1以上のH原子は、Fで置き代えられてよい。)であり;ここで二個以上の置換基R3は、モノあるいはポリ環式の脂肪族もしくは芳香族環構造を互いに形成してもよく;
ただし、8個の基TおよびUの少なくとも一つは、各場合に、少なくとも一つの5〜60個の環原子を有する芳香族および/または複素環式芳香族基を含む置換基R1を含む。
Xは、出現毎に同一であるか異なり、CR2およびNであることができるが、ただし、少なくとも一つのXは、CR2であり、CR2からの少なくとも一つのR2は、Zであり、ここで、Zは、置換基であり、多数回出現するならば互いに独立して、5〜60個の環原子を有する一以上の芳香族および/または複素環式芳香族環および/または環構造を含み、
および
n、mは、0、1、2,3または4の整数であり、
ここで、六員環がn回出現する場合には、基Tのnは、CR1であり、n個の六員環は、CR1のR1に置き代わり、六員環がm回出現する場合には、基Uのmは、CR1であり、m個の六員環は、CR1のR1に置き代わる。
・式(30)を有する化合物中で、多くて6個、好ましくは、4個以下であり、非常に、好ましくは、3個以下であり、非常に、特に、好ましくは、2個以下であり、
・式(31)を有する化合物中で、多くて4個、好ましくは、4個以下であり、非常に、好ましくは、3個以下であり、非常に、特に、好ましくは、2個以下であり、
・式(32)を有する化合物中で、多くて7個、好ましくは、4個以下であり、非常に、好ましくは、3個以下であり、非常に、特に、好ましくは、2個以下であり、および
・式(33)を有する化合物中で、多くて8個、好ましくは、4個以下であり、非常に、好ましくは、3個以下であり、非常に、特に、好ましくは、2個以下である。
および、ただし、少なくとも一つのXは、CR2であり、CR2からの少なくとも一つのR2は、Zであり、ここで、Zは、既に上記に定義したとおり、置換基であり、一個以上出現するならば、互いに独立して、5〜60個の環原子を有する一以上の芳香族および/または複素環式芳香族環および/または環構造を含み;
二個以上の基R2は、C-CもしくはC-N連結反応条件下で重合する同一であるか異な官能基である。
混合物は、個々のエミッターのためのまたはエミッター混合物のためのマトリックス材料として使用することができる。
以下の合成は、特に断らなければ、保護ガス雰囲気下、無水溶媒中で行われる。出発物質(I)、(III)、(V)、(XVII)および(XX)と溶媒は、商業的に入手可能である(VWR, Sigma-Aldrich)。化合物(XI)(CAS [3842-55-5])は、H. Zhong et al., Organic Letters, 2008, Vol. 10, 709-712と同様にして調製することができる。化合物(XIII)((CAS [88590-00-5])は、M. Tavasli et al.; Synthesis; 2005; 1619-1624と同様にして調製することができる。化合物(XV)は、WO2010/136109に記載されたプロセスと同様にして調製することができる。化合物(XXV)は、DE102009041414.2に記載されたプロセスと同様にして調製することができる。化合物(XXXII)は、Kim et al., Molecular Crystals and Liquid Crystals, 2008, 491,133-144と同様にして調製することができる。
化合物(II)〜(XII)の調製
62.0g(300ミリモル)のピレン(I)が、1000mlのジクロロメタンと1000mlのアセトニトリル中に溶解される。525g(2.254ミリモル)の過ヨウ素酸ナトリウム、1200mlの蒸留水と7.6g(36ミリモル)の三塩化ルテニウムが添加される。暗茶色の溶液は、40℃で一晩中撹拌され、引き続き、蒸留水(4000ml)に添加され、沈殿物は水で洗浄される。濾過物の有機相は、分離され、水性相はジクロロメタンで何度も抽出される。ジクロロメタン中に溶解された有機相と沈殿物は、結合され、硫酸ナトリウム溶液(10%)で洗浄される。溶媒は、減圧下除去される。固形物は、クロロベンゼンから再結晶化される。収率は、32.63g(139.8ミリモル)で、理論値の45%に対応する。
32.63g(139.8ミリモル)の化合物(II)と31.08g(147.4ミリモル)の1,3-ジフェニルアセトン(III)が、4500mlのメタノール中に溶解される。オレンジ色の懸濁液が還流下加熱され、メタノール(31ml)中の水酸化カリウム溶液(7.76g)がゆっくりと滴下される。即座に、黒紫色化が起こる。混合物は、還流下60min加熱され、引き続き、室温で一晩中撹拌される。濾過後、沈殿物は冷メタノールで洗浄され、減圧下乾燥され、さらなる精製をすることなく反応される。収率は、41.89g(103.1ミリモル)で、理論値の73%に対応する。
アルゴン雰囲気下、41.89g(103.1ミリモル)の化合物(IV)、27.96g(154.6ミリモル)のm-ブロモフェニルアセチレン(V)と533mlのデカヒドロ-2-ナフトールが、フラスコ中に導入され、180℃で2時間加熱される。反応溶液の短時間冷却後、533mlのクロロベンゼンが添加される。反応溶液は、再び室温になるまで撹拌される。引き続き、5000mlのメタノールが添加され、一晩冷蔵庫におかれる。薄緑色の溶液は薄黄色の沈殿物を含み、沈殿物はジクロロメタンの添加により溶解され、溶液はオレンジブラウン色を有する。溶媒は減圧下除去され、ベージュ色の粗生成物が得られ、さらなる精製をすることなく反応される。収率は、50.72g(91.0ミリモル)で、理論値の88%に対応する。
50.72g(91.0ミリモル)の化合物(VI)、91.03g(422.1ミリモル)の過ヨウ素酸ナトリウムと1.92g(9.0ミリモル)の水含有三塩化ルテニウムが、フラスコ中に導入される。3100mlのジクロロメタンと3100mlのアセトニトリルが添加されるが、固形物の完全な溶解は生じない。懸濁液は、30℃で6.5時間撹拌され、茶黒色の溶液が引き続き、存在する。反応は、6000mlの蒸留水の添加により終了し、暗茶色の沈殿物が観察される。反応バッチは、一晩冷蔵庫に貯蔵される。水性相が、引き続き、デカントされ、沈殿物は、ジクロロメタン中に溶解される。有機相が分離され、水性相はジクロロメタンで三度抽出される。結合した有機相は、引き続き、蒸留水で二度、10%硫酸ナトリウム溶液で一度、(飽和)塩化ナトリウム溶液で一度連続的に洗浄される。溶媒は減圧下除去され、得られた膜状の固形物は、さらに直接反応される。収率は、40.22g(68.3ミリモル)で、理論値の75%に対応する。
40.22g(68.3ミリモル)の化合物(VII)と16.21g(71.6ミリモル)の1,3-ジフェニルアセトン(III)が、768mlのメタノール中に溶解される。オレンジ色の懸濁液が還流下加熱され、メタノール(1922ml)中の水酸化カリウム溶液(4.28g)がゆっくりと滴下される。遅れて変色が起こり、オリーブグリーン色に着色し、茶色の沈殿物が生成する。反応バッチは、還流下2時間加熱され、引き続き、一晩冷蔵庫に貯蔵される。濾過後、沈殿物は冷メタノールで洗浄され、減圧下乾燥され、さらに直接反応される。収率は、24.97g(32.7ミリモル)で、理論値の48%に対応する。
アルゴン雰囲気下、24.97g(32.7ミリモル)の化合物(VIII)、8.87g(49.1ミリモル)のm-ブロモフェニルアセチレン(V)と3360mlのデカヒドロ-2-ナフトールが、フラスコ中に導入され、180℃で2時間加熱される。反応混合物は、減圧下除去される。粗生成物は、トルエンによる熱抽出により精製される。収率は、16.14g(17.6ミリモル)で、理論値の54%に対応する。
16.14g(17.6ミリモル)の化合物(IX)、9.84g(38.74ミリモル)のビス(ピナコラート)ジボランと10.37g(105.6ミリモル)の酢酸カリウムが、269mlのジオキサン中に懸濁される。718.90mg(0.9ミリモル)の1,1-ビス(ジフェニルホスフィノ)フェロセンパラジウム(II)ジクロリド*DCMが、この懸濁液に添加され、反応混合物は、還流下16h加熱される。有機相は、水で何度も抽出される。溶媒は減圧下除去される。固形物は、アセトニトリル/トルエンから再結晶化される。収率は、11.03g(10.9ミリモル)で、理論値の62%に対応する。
11.03g(10.9ミリモル)の化合物(X)、5.84g(21.8ミリモル)の化合物(XI)と2.54g(24.1ミリモル)の炭酸ナトリウムが、716mlのトルエンと716mlのジオキサンと286mlの水中に懸濁される。642.46mg(0.56ミリモル)のテトラキス(トリフェニルホスフィン)パラジウム(0)が、この懸濁液に添加され、混合物は、引き続き、還流下22h加熱される。冷却後、有機相は、分離され、286mlの水で三度、286mlの飽和塩化ナトリウム溶液で一度洗浄され、硫酸ナトリウムを使用して乾燥され、引き続き、蒸発乾固される。得られた固形物は、トルエンから二度される。収率は、10.53g(8.62ミリモル)で、理論値の79%に対応する。
化合物(VIV)の調製:
化合物(XVI)の調製
化合物(XVIII)〜(XXIV)の調製
化合物(XXIV)の調製のための合成手順:
化合物(XVIII)の合成は、m-ブロモフェニルアセチレンを15.80g(154.6ミリモル)のフェニルアセチレンに置き代えて、41.89g(103.1ミリモル)の9,11-ジフェニルシクロペンタ[e]ピレン-10-オンによる化合物(VI)の合成と同じように実行される。収率は、43.59g(90.8ミリモル)で、理論値の88%に対応する。
化合物(XIX)の合成は、43.59g(90.8ミリモル)の9,10,12-トリフェニルベンゾ[e]ピレンによる化合物(VII)の合成と同じように実行される。収率は、32.43g(63.5ミリモル)で理論値の70%に対応する。
化合物(XXI)の合成は、1,3-ジフェニルアセトンを25.60g(66.7ミリモル)の1,3-ビス(3-ブロモフェニル)アセトンに置き代えて、32.43g(63.5ミリモル)の9,10,12-トリフェニルベンゾ[e]ピレン-4,5-ジオンによる化合物(VIII)の合成と同じように実行される。収率は、24.07g(28.68ミリモル)で、理論値の45%に対応する。
化合物(XXII)の合成は、m-ブロモフェニルアセチレンを4.38g(42.9ミリモル)のフェニルアセトンに置き代えて、24.07g(28.6ミリモル)の化合物(XXI)による化合物(IX)の合成と同じように実行される。収率は、11.51g(12.6ミリモル)で、理論値の44%に対応する。
化合物(XXIII)の合成は、11.51g(12.6ミリモル)の化合物(XXII)による化合物(X)の合成と同じように実行される。収率は、7.62g(7.7ミリモル)で、理論値の60%に対応する。
化合物(XXIV)の合成は、7.62g(7.6ミリモル)の化合物(XXIII)による化合物(XII)の合成と同じように実行される。収率は、7.23g(5.9ミリモル)で、理論値の78.5%に対応する。
化合物(XXVI)の調製
化合物(XXVI)の調製のための合成手順:
化合物(XXVII)〜(XXXIII)の調製
化合物(XVIII)の合成は、1,3-ジフェニルアセトンを56.65g(147.5ミリモル)の1,3-ビス(3-ブロモフェニル)アセトンに置き代えて、32.63g(139.8ミリモル)の化合物(II)による化合物(IV)の合成と同じように実行される。収率は、57.08g(101.2ミリモル)で、理論値の72%に対応する。
化合物(XXVIII)の合成は、m-ブロモアセチレンを25.32g(171.5ミリモル)のフェニルアセチレンに置き代えて、57.08g(101.2ミリモル)の化合物(XXVII)による化合物(VI)の合成と同じように実行される。収率は、56,85g(89.1ミリモル)で、理論値の88%に対応する。
化合物(XXIX)の合成は、56.85g(89.1ミリモル)の化合物(XXVIII)9による化合物(VII)の合成と同じように実行される。収率は、38.72g(57.9ミリモル)で、理論値の65%に対応する。
化合物(XXX)の合成は、1,3-ジフェニルアセトンを23.35g(60.8ミリモル)の1,3-ビス(3-ブロモフェニル)アセトンに置き代えて、38.72g(57.9ミリモル)の化合物(XXIX)による化合物(VIII)の合成と同じように実行される。収率は、29.01g(29.0ミリモル)で、理論値の50%に対応する。
化合物(XXXI)の合成は、m-ブロモアセチレンを4.44g(43.5ミリモル)のフェニルアセチレンに置き代えて、29.01g(29.0ミリモル)の化合物(XXX)による化合物(IX)の合成と同じように実行される。収率は、16.89g(15.7ミリモル)で、理論値の54%に対応する。
化合物(XXXIII)の合成は、2-クロロ-4,6-ジフェニル-1,3,5-トリアジンを24.97g(67.6ミリモル)の9-フェニル-3-(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)-9Hカルバゾールに置き代えて、16.89g(15.7ミリモル)の化合物(XXXI)による化合物(XII)の合成と同じように実行される。収率は、9.49g(5.5ミリモル)で、理論値の35%に対応する。
化合物(XXXIV)〜(XXXVIII)の調製
化合物(XXXIV)の合成は、38.72g(58.0ミリモル)の化合物(XXIX)による化合物(X)の合成と同じように実行される。収率は、28.73g(37.7ミリモル)で、理論値の65%に対応する。
合成は、27.73g(37.7ミリモル)の化合物34による化合物(XII)と同じように実行される。収率は、29.35g(30.2ミリモル)で、理論値の80%に対応する。
化合物(XXXVI)の合成は、29.35g(30.2ミリモル)の化合物(XXXV)による化合物(VIII)の合成と同じように実行される。収率は、18.39g(16.0ミリモル)で、理論値の53%に対応する。
化合物(XXXVII)の合成は、18.39g(16.0ミリモル)の化合物(XXXVI)による化合物(IX)の合成と同じように実行される。収率は、8.10g(6.2ミリモル)で、理論値の39%に対応する。
化合物(XXXVIII)の合成は、2-フェニル-9H-カルバゾールを3.88g(13.7ミリモル)の12,12-ジメチル-10,12-ジヒドロ-10-アザインデノ[2,1-b]フルオレンに置き代えて、8.10g(6.2ミリモル)の化合物(XXXVII)による化合物(XIV)の合成と同じように実行される。収率は、5.15g(4.5ミリモル)で、理論値の55%に対応する。
本発明の化合物を含む燐光有機エレクトロルミネッセンス素子の製造と特性決定
エミッターTE-1(WO2004/085449にしたがって合成)の構造が、明確さのために、以下に示される。
Claims (14)
- 式(30)の化合物:
R2は、出現毎に同一であるか異なり、H、または、以下の式(34)〜(46)を有する基の群から選ばれ、ただし、少なくとも一つのR 2 は、以下の式(34)〜(46)を有する基の群から選ばれ、
R1は、出現毎に同一であるか異なり、H、または、5〜60個の芳香族環原子を有する芳香族環もしくは複素環式芳香族環であり、
R3は、出現毎に同一であるか異なり、H、D、Fまたは1〜40個のC原子を有する脂肪族もしくは芳香族炭化水素基および/または複素環式芳香族基(さらに、1以上のH原子は、Fで置き代えられてよい。)であり;ここで二個以上の置換基R3は、モノあるいはポリ環式の脂肪族もしくは芳香族環構造を互いに形成してもよい。 - 環毎の二個の基R2の最大一個は、式(34)〜(46)を有する基の群から選ばれ、他方はHであることを特徴とする、請求項1記載の化合物。
- 少なくとも一つの請求項1または2記載の化合物と少なくとも一つの溶媒を含む調合物。
- 少なくとも一つの請求項1または2記載の化合物と、エミッター、ホスト材料、マトリックス材料、電子輸送材料(ETM)、電子注入材料(EIM)、正孔輸送材料(HTM)、正孔注入材料(HIM)、電子障壁材料(EBM)、正孔障壁材料(HBM)、励起子障壁材料(ExBM)の群から選ばれる少なくとも一つのさらなる有機機能性材料を含む組成物。
- 少なくとも一つのさらなる有機機能性材料がエミッターである請求項4記載の組成物。
- 少なくとも一つのさらなる有機機能性材料が蛍光および/または燐光エミッターである請求項4記載の組成物。
- 少なくとも一つの請求項1または2記載の化合物または請求項3記載の調合物または請求項4〜6何れか1項記載の組成物の、電子素子での使用。
- 電子素子が、有機エレクトロルミネッセンス素子(OLED、PLED)、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)、有機光学検査素子、有機光受容素子、有機電場消光素子(O-FQD)、発光電子化学電池(LEC)もしくは有機レーザーダイオード(O-laser)より成る群から選ばれる請求項7記載の使用。
- 少なくとも一つの請求項1または2記載の化合物または請求項3記載の調合物または請求項4〜6何れか1項記載の組成物を含む電子素子。
- 電子素子が、有機エレクトロルミネッセンス素子(OLED、PLED)、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)、有機光学検査素子、有機光受容素子、有機電場消光素子(O-FQD)、発光電子化学電池(LEC)もしくは有機レーザーダイオード(O-laser)より成る群から選ばれる請求項9記載の電子素子。
- 少なくとも一つの請求項1または2記載の化合物が、一以上の発光層中でホストもしくはマトリックス材料として使用されることを特徴とする有機エレクトロルミネッセンス素子。
- 少なくとも一つの請求項1または2記載の化合物が、エミッターと組み合わせて使用されることを特徴とする請求項11記載の有機エレクトロルミネッセンス素子。
- エミッターは、蛍光または燐光エミッターであることを特徴とする請求項12記載の有機エレクトロルミネッセンス素子。
- 医療での光治療での使用のための請求項9〜12何れか1項記載の有機エレクトロルミネッセンス素子。
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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 |
DE102008056688A1 (de) | 2008-11-11 | 2010-05-12 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009022858A1 (de) | 2009-05-27 | 2011-12-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
DE102009005746A1 (de) | 2009-01-23 | 2010-07-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
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 |
DE102009041414A1 (de) | 2009-09-16 | 2011-03-17 | Merck Patent Gmbh | Metallkomplexe |
US20120245658A1 (en) * | 2009-12-09 | 2012-09-27 | Merck Patent Gmbh | Therapeutic and Cosmetic Electroluminescent Compositions |
JP2013123000A (ja) | 2011-12-12 | 2013-06-20 | Sony Corp | 固体撮像装置およびその製造方法 |
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2011
- 2011-02-12 DE DE102011011104A patent/DE102011011104A1/de not_active Withdrawn
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2012
- 2012-01-18 US US13/984,552 patent/US9029425B2/en not_active Expired - Fee Related
- 2012-01-18 WO PCT/EP2012/000205 patent/WO2012107163A1/de active Application Filing
- 2012-01-18 EP EP12700615.3A patent/EP2673249B1/de active Active
- 2012-01-18 JP JP2013552869A patent/JP6230916B2/ja active Active
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EP2673249A1 (de) | 2013-12-18 |
WO2012107163A1 (de) | 2012-08-16 |
US20130317475A1 (en) | 2013-11-28 |
US9029425B2 (en) | 2015-05-12 |
EP2673249B1 (de) | 2019-04-03 |
DE102011011104A1 (de) | 2012-08-16 |
JP2014513040A (ja) | 2014-05-29 |
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