JP5795320B2 - 有機エレクトロルミネッセンス素子のための材料 - Google Patents
有機エレクトロルミネッセンス素子のための材料 Download PDFInfo
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- JP5795320B2 JP5795320B2 JP2012539207A JP2012539207A JP5795320B2 JP 5795320 B2 JP5795320 B2 JP 5795320B2 JP 2012539207 A JP2012539207 A JP 2012539207A JP 2012539207 A JP2012539207 A JP 2012539207A JP 5795320 B2 JP5795320 B2 JP 5795320B2
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- 239000000463 material Substances 0.000 title claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 129
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 31
- 239000011159 matrix material Substances 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 18
- 230000004888 barrier function Effects 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000002019 doping agent Substances 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000304 alkynyl group Chemical group 0.000 claims description 5
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 3
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 238000005401 electroluminescence Methods 0.000 claims description 3
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- HSSKSBDTYLXIDN-UHFFFAOYSA-N (3,5-dibromophenyl)-phenylmethanone Chemical compound BrC1=CC(Br)=CC(C(=O)C=2C=CC=CC=2)=C1 HSSKSBDTYLXIDN-UHFFFAOYSA-N 0.000 claims description 2
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- COEJCDOAIXEITB-UHFFFAOYSA-N [Li]C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Li]C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 COEJCDOAIXEITB-UHFFFAOYSA-N 0.000 claims description 2
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- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 6
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 5
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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Images
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
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Description
Xは、出現毎に同一であるか異なり、CR1またはNであり、ここで、各環中の最大三個のXは、Nであり、
Aは、出現毎に同一であるか異なり、CR2またはNであり、ここで、各環中の最大三個のAは、Nであり、
R1、R2は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(R4)3、Si(R4)3、B(OR4)2、C(=O)R4、P(=O)(R4)2、S(=O)R4、S(=O)2R4、-CR4=CR4-、OSO2R4、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、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原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R4により置換されてよく、1以上の隣接しないCH2基は、R4C=CR4、C≡C、Si(R4)2、Ge(R4)2、Sn(R4)2、C=O、C=S、C=Se、C=NR4、P(=O)(R4)、SO、SO2、NR4、O、SもしくはCONR4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、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、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ラルキルもしくはヘテロアラルキル基であり;ここで、2個以上の隣接する置換基R1は、それらが結合する原子と一緒にまたは2個以上の隣接する置換基R2は、それらが結合する原子と一緒に、モノ-あるいはポリ環状脂肪族もしくは芳香族環構造を形成してもよく;
Xに結合する少なくとも一つの置換基R1は、1以上の基R4により置換されてよいトリアジンであることを特徴とし、
または、少なくとも一つの置換基R2は、1以上の基R4により置換されてよい六員環複素環式芳香族環構造であり、および、少なくとも一つのR1は、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であることを特徴とし、
R3は、出現毎に同一であるか異なり、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またはこれらの構造の組み合わせであり、
R4は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(R5)3、Si(R5)3、B(OR5)2、C(=O)R5、P(=O)(R5)2、S(=O)R5、S(=O)2R5、-CR5=CR5-、OSO2R5、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、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原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R5により置換されてよく、1以上の隣接しないCH2基は、R5C=CR5、C≡C、Si(R5)2、Ge(R5)2、Sn(R5)2、C=O、C=S、C=Se、C=NR5、P(=O)(R5)、SO、SO2、NR5、O、SもしくはCONR5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R5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、1以上の基R5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、1以上の基R5で置換されてよい5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基であり;ここで、2個以上の基R4は、それらが結合する原子と一緒に、互いに、モノ-あるいはポリ環状脂肪族もしくは芳香族環構造を形成してもよく;
R5は、出現毎に同一であるか異なり、1〜20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であり;ここで、2個以上の基R5は、これらが結合する原子と一緒に互いに互いに、モノ-あるいはポリ環状、脂肪族もしくは芳香族環構造を形成してもよい。
式(1)の化合物が、発光層中で発光化合物のためのマトリックス材料として使用されるならば、一以上の燐光材料(トリプレットエミッター)と組み合わせて使用することができる。本発明の意味での燐光発光は、比較的高いスピン多重度、すなわち>1のスピン状態を有する励起状態から、特に、励起三重項状態からのルミネッセンスを意味するものと解される。本発明の目的のために、すべてのルミネッセンス遷移金属錯体とすべてのルミネッセンスランタノイド錯体、特に、ルミネッセンスイリジウム、白金、オスミウム、金および銅化合物は、燐光発光材料と呼ばれる、そこで、式(1)の化合物と発光化合物の混合物は、エミッターとマトリックス材料の全混合物を基礎として、99〜1重量%、好ましくは、98〜10重量%、特に、好ましくは、97〜60重量%、特に、95〜75重量%の式(1)化合物を含む。対応して、混合物は、エミッターとマトリックス材料の全混合物を基礎として、1〜99重量%、好ましくは、2〜90重量%、特に、好ましくは、3〜40重量%、特に、5〜25重量%のエミッターを含む
適切な燐光化合物(三重項エミッター)は、適切な励起により、好ましくは、可視域で発光する化合物を含み、加えて、20より大で、好ましくは、38より大で、84より小な、特に好ましくは、56より大で、80より小な原子番号を有する少なくとも一つの原子を含む。使用される燐光発光エミッターは、好ましくは、銅、モリブデン、タングステン、レニウム、ルテニウム、オスミウム、ロジウム、イリジウム、パラジウム、白金、銀および金またはユウロピウムを含む化合物、特に、イリジウムもしくは白金を含む化合物である
上記エミッターの例は、出願WO 00/70655、WO 01/41512、WO 02/02714、WO 02/15645、EP1191613、EP1191612、EP1191614、WO 05/033244、WO 05/019373、US2005/0258742、 WO 09/146770、WO 10/015307、WO 10/031485、WO 10/054731およびWO 10/054728により明らかにされる。さらに適切なものは、たとえば、DE 102009007038.9、DE 102009011223.5およびDE 102009013041.1にしたがう錯体である。一般的に燐光OLEDに対して先行技術にしたがって使用され、有機エレクトロルミネッセンス素子の分野の当業者に知られるあらゆる燐光化合物が適切であり、当業者は進歩性を必要とすることなく、さらなる燐光錯体を使用することができる。
以下の合成は、他に断らない限り、保護ガス雰囲気下で、無水溶媒中で行われる。出発物質8と溶媒はたとえば、アルドリッチ(ALDRICH)から商業的に入手可能である。化合物1と5は、WO 09/124627にしたがって調製することができる。化合物2は、J. Mater. Chem. 2007, 17, 3714-3719と同様に調製することができる。
850mlのジメチルスルホキシド、25.18g(1.1モル当量、0.099ミリモル)のビス(ピナコラート)ジボランと25.66g(2.9モル当量、0.261ミリモル)の酢酸カリウムが、35.0g(1モル当量0.090ミリモル)の化合物2、2.25g(3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)クロライド(ジクロロメタン(1:1)、Pd13%の錯体)が、引き続き、添加される。バッチは、100℃で3時間加熱され、ついで、室温まで冷却され、400mlの水が添加される。混合物は、酢酸エチルで抽出され、結合した有機相は、ついで、硫酸ナトリウムで乾燥され、減圧下蒸発される。精製は、再結晶化(ヘプタン)により実行され、ベージュ色の固形物(81.3%)を得る。
10.97g(1モル当量、0.017ミリモル)の化合物1、33.14g(4.4モル当量、0.076ミリモル)の化合物3と29.42g(8.0モル当量0.139ミリモル)の燐酸三カリウムが、250mlのトルエン、125mlのジオキサンと325mlの水中に懸濁される。1.270g(4.2ミリモル)のトリ-o-トリルホスフィンと、ついで、0.156g(0.7ミリモル)の酢酸パラジウム(II)が、この懸濁液に添加され、反応混合物は40時間還流下加熱される。冷却後、有機相は分離される。水性相は、ジクロロメタンで抽出され、結合した有機相は、ついで、硫酸ナトリウムで乾燥され、ろ過され、減圧下蒸発される。残留物は、ジメチルホルムアミドから再結晶化され、熱トルエンで抽出される。収率は、9.4g(6.1ミリモル)で、理論値の35.1%に対応する。
20g(32.1ミリモル)の化合物5が、3.4g(19.2ミリモル)の沃素酸と4.9g(19.2ミリモル)の沃素とともに、10mlのクロロホルムと50mlの氷酢酸中に懸濁され、混合物は、80℃で加熱される。TLCチェック後、バッチは、室温まで冷却され、250mlの水が添加される。混合物は、塩化メチレンで抽出され、結合した有機相は、ついで、硫酸ナトリウムを使用して乾燥され、ろ過され、減圧下蒸発される。精製は、洗浄(エタノール)と再結晶化(トルエン/酢酸エチル)により実行され、無色の固形物(15.3g、理論値の64%)を得る。
化合物7の合成が、化合物3と同様に実行される。収率は、7.0g(9.2ミリモル)で理論値の46%に対応する。
化合物9の合成が、化合物4と同様に実行される。収率は、4.48g(5.2ミリモル)で理論値の57%に対応する。
化合物10の合成が、化合物1と同様に実行される。79.8g(理論値の91.9%)の固形物が得られる。
10.0g(1モル当量、21ミリモル)の化合物10、20.1g(2.2モル当量、46ミリモル)の化合物3と53.3g(11.9モル当量、251ミリモル)の燐酸三カリウムが、200mlのトルエン、200mlのジオキサンと200mlの水中に懸濁される。この混合物は、アルゴンを使用して15分間脱気され、458mg(1.50ミリモル)のトリ-o-トリルホスフィンと、ついで、230mg(1.03ミリモル)の酢酸パラジウム(II)が、ついで、添加される。反応混合物は、16時間還流下加熱され、その間に白色沈殿物が堆積する。冷却後、0.60lの水と1lのジクロロメタンが添加され、有機相は分離される。有機相は、水で三度洗浄される。結合した有機相は、減圧下溶媒から解放される。得られた残留物は、200mlの熱エタノールで撹拌され、吸引ろ過され、さらなるエタノールで洗浄され、実質的に無色の固形物が残る。ジオキサンからの再結晶化により、1.90g(2.04ミリモル、理論値の96.5%)の無色の固形物を得る。
化合物12の合成が、化合物3と同様に実行される。収率は、590mg(1.04ミリモル)で理論値の25%に対応する。
化合物14の合成が、化合物8と同様に実行される。6.80g(9.39ミリモル、理論値の27%)のベージュ色の固形物が得られる。
化合物15の合成が、化合物11と同様に実行される。収率は、8.00g(47.0ミリモル)で理論値の66%に対応する。
TEG(WO 04/026886にしたがって合成)、TMM-1(DE 102008036982.9にしたがって合成)とTMM-2(WO 09/124627にしたがって合成)と、本発明によるTMM-3〜6の化合物は、明確さのために、以下に示される。
Claims (15)
- 式(19)の化合物。
R1、R2は、出現毎に同一であるか異なり、H、D、Cl、Br、I、F、CN、NO2、N(R4)3、Si(R4)3、B(OR4)2、C(=O)R4、P(=O)(R4)2、S(=O)R4、S(=O)2R4、-CR4=CR4-、OSO2R4、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、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原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R4により置換されてよく、1以上の隣接しないCH2基は、R4C=CR4、C≡C、Si(R4)2、Ge(R4)2、Sn(R4)2、C=O、C=S、C=Se、C=NR4、P(=O)(R4)、SO、SO2、NR4、O、SもしくはCONR4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、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、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ラルキルもしくはヘテロアラルキル基であり;ここで、2個以上の隣接する置換基R1は、それらが結合する原子と一緒にまたは2個以上の隣接する置換基R2は、それらが結合する原子と一緒に、モノ-あるいはポリ環状脂肪族もしくは芳香族環構造を互いに形成してもよく;
少なくとも一つのR1は、1以上の基R4により置換されてよいトリアジンを含むことを特徴とし、または、少なくとも一つのR2は、1以上の基R4により置換されてよい六員環複素環式芳香族環構造であり、および、少なくとも一つのR1は、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であることを特徴とし、
R4は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(R5)3、Si(R5)3、B(OR5)2、C(=O)R5、P(=O)(R5)2、S(=O)R5、S(=O)2R5、CR5=CR5、OSO2R5、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、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原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R5により置換されてよく、1以上の隣接しないCH2基は、R5C=CR5、C≡C、Si(R5)2、Ge(R5)2、Sn(R5)2、C=O、C=S、C=Se、C=NR5、P(=O)(R5)、SO、SO2、NR5、O、SもしくはCONR5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R5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、1以上の基R5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、1以上の基R5で置換されてよい5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基であり;ここで、2個以上の基R4は、それらが結合する原子と一緒に互いに、モノ-あるいはポリ環状脂肪族もしくは芳香族環構造を形成してもよく;
R5は、出現毎に同一であるか異なり、1〜20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であり;ここで、2個以上の基R5は、それらが結合する原子と一緒に互いに、モノ-あるいはポリ環状、脂肪族もしくは芳香族環構造を形成してもよい。) - 少なくとも一つの基R1が、トリアジンであるならば、これは、各場合に、1以上の基R4により置換されてよい1,3,5-トリアジンもしくは1,2,4-トリアジンであり、ここで、基R4は、水素もしくは重水素ではないことを特徴とし、;または、少なくとも一つの基R2が、六員環複素環式芳香族基であるならば、夫々が1以上の基R4により置換されてよいトリアジン、ピリミジン、ピラジン、ピリダジンもしくはピリジンから選ばれ、ここで、基R4は、水素もしくは重水素ではないことを特徴とする、請求項1記載の化合物。
- 基R4は、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2記載の化合物。
- ビス(3,5-ジブロモ)ベンゾフェノンと、置換あるいは非置換2-リチオビフェニル、2-リチオジフェニルエーテル、2-リチオジフェニルチオエーテル、2-(2-リチオフェニル)-2-フェニル-1,3-ジオキサン、2-リチオフェニルジフェニルアミンもしくは対応するグリニャール化合物とを反応させて、トリアリールメタノールを得、酸性条件下の環化が続き、随意に、臭素基のさらなる反応に続くことを含む、請求項1〜5何れか1項記載の化合物の製造方法。
- 請求項1〜5何れか1項記載の少なくとも一つの化合物と少なくとも一つのさらなる化合物を含む混合物。
- 少なくとも一つのさらなる化合物が、蛍光もしくは燐光ドーパントである請求項7記載の混合物。
- 請求項1〜5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7または8記載の混合物と一以上の溶媒を含む調合物。
- 溶媒が、有機溶媒である請求項9記載の調合物。
- 請求項1〜5何れか1項記載の化合物または請求項7または8記載の混合物の、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である請求項11記載の使用。
- 請求項1〜5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7または8記載の混合物を含む、電子素子。
- 電子素子は、有機エレクトロルミネッセンス素子(OLED、PLED)、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)、有機集積回路(O-IC)、有機太陽電池(O-SC)、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)または有機光受容器より成る群から選ばれる、請求項13記載の電子素子。
- 請求項1〜5何れか1項記載の化合物が、発光層中で、随意にさらなるマトリックス材料との混合物として、蛍光もしくは燐光化合物のためのマトリックス材料としておよび/または請求項1〜5何れか1項記載の化合物が、電子輸送層または正孔障壁層中で電子輸送材料としてまたは正孔障壁材料として使用され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ネッセンス素子。
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US20120228554A1 (en) | 2012-09-13 |
JP2013510889A (ja) | 2013-03-28 |
US10233159B2 (en) | 2019-03-19 |
US10981880B2 (en) | 2021-04-20 |
DE102009053644B4 (de) | 2019-07-04 |
WO2011060859A1 (de) | 2011-05-26 |
DE102009053644A1 (de) | 2011-05-19 |
US20190169139A1 (en) | 2019-06-06 |
TW201134786A (en) | 2011-10-16 |
US20210221775A1 (en) | 2021-07-22 |
US11760734B2 (en) | 2023-09-19 |
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