JPWO2019220276A1 - 有機化合物、発光素子、発光装置、電子機器、照明装置および電子デバイス - Google Patents
有機化合物、発光素子、発光装置、電子機器、照明装置および電子デバイス Download PDFInfo
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- JPWO2019220276A1 JPWO2019220276A1 JP2020519207A JP2020519207A JPWO2019220276A1 JP WO2019220276 A1 JPWO2019220276 A1 JP WO2019220276A1 JP 2020519207 A JP2020519207 A JP 2020519207A JP 2020519207 A JP2020519207 A JP 2020519207A JP WO2019220276 A1 JPWO2019220276 A1 JP WO2019220276A1
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- WOYDRSOIBHFMGB-UHFFFAOYSA-N n,9-diphenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 WOYDRSOIBHFMGB-UHFFFAOYSA-N 0.000 description 1
- BBNZOXKLBAWRSH-UHFFFAOYSA-N n,9-diphenyl-n-[4-(10-phenylanthracen-9-yl)phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 BBNZOXKLBAWRSH-UHFFFAOYSA-N 0.000 description 1
- NCCYEOZLSGJEDF-UHFFFAOYSA-N n,n,9-triphenyl-10h-anthracen-9-amine Chemical compound C12=CC=CC=C2CC2=CC=CC=C2C1(C=1C=CC=CC=1)N(C=1C=CC=CC=1)C1=CC=CC=C1 NCCYEOZLSGJEDF-UHFFFAOYSA-N 0.000 description 1
- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 1
- RVHDEFQSXAYURV-UHFFFAOYSA-N n-[4-(9,10-diphenylanthracen-2-yl)phenyl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=C3C(C=4C=CC=CC=4)=C4C=CC=CC4=C(C=4C=CC=CC=4)C3=CC=2)C=C1 RVHDEFQSXAYURV-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- COVCYOMDZRYBNM-UHFFFAOYSA-N n-naphthalen-1-yl-9-phenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N1C2=CC=C(N(C=3C=C4C5=CC=CC=C5N(C=5C=CC=CC=5)C4=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 COVCYOMDZRYBNM-UHFFFAOYSA-N 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 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
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- HYXGAEYDKFCVMU-UHFFFAOYSA-N scandium oxide Chemical compound O=[Sc]O[Sc]=O HYXGAEYDKFCVMU-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- PBCFLUZVCVVTBY-UHFFFAOYSA-N tantalum pentoxide Inorganic materials O=[Ta](=O)O[Ta](=O)=O PBCFLUZVCVVTBY-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 238000007736 thin film deposition technique Methods 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- CMLWFCUAXGSMBB-UHFFFAOYSA-N tris(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C=1C(=CC=CC=1OC)OC)C1=C(OC)C=CC=C1OC CMLWFCUAXGSMBB-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- ZVWKZXLXHLZXLS-UHFFFAOYSA-N zirconium nitride Chemical compound [Zr]#N ZVWKZXLXHLZXLS-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
Description
を有する電子機器である。
有機EL素子に用いることが可能なキャリア輸送性を有する有機化合物の中でも、屈折率が小さい材料の一つとして1,1−ビス−(4−ビス(4−メチル−フェニル)−アミノ−フェニル)−シクロヘキサン(略称:TAPC)が知られている。屈折率の小さな材料をEL層に用いることで、高い外部量子効率を示す発光素子を得ることが可能であるため、TAPCを用いることで良好な外部量子効率を有する発光素子が得られることが期待される。しかし一方で、TAPCには耐熱性が低く、信頼性的に不利であるという問題があった。
図1に、本発明の一態様の発光素子を表す図を示す。本発明の一態様の発光素子は、第1の電極101と、第2の電極102、EL層103を有し、当該EL層に実施の形態1で示した有機化合物を用いている。
本実施の形態では、実施の形態2に記載の発光素子を用いた発光装置について説明する。
本実施の形態では、実施の形態2に記載の発光素子を照明装置として用いる例を図6を参照しながら説明する。図6(B)は照明装置の上面図、図6(A)は図6(B)におけるe−f断面図である。
本実施の形態では、実施の形態2に記載の発光素子をその一部に含む電子機器の例について説明する。実施の形態2に記載の発光素子は発光効率が良好であり、消費電力の小さい発光素子である。その結果、本実施の形態に記載の電子機器は、消費電力が小さい発光部を有する電子機器とすることが可能である。
本実施例では、本発明の一態様である有機化合物、4,4’−(1,1−シクロヘキサン−ジイル)ビス[N,N−ビス(4−シクロヘキシルベンゼン−1−イル)アミノベンゼン](略称:TAPC−02)の合成方法について説明する。なお、TAPC−02の構造を以下に示す。
三口フラスコに1,1−ビス(4−アミノフェニル)シクロヘキサン5.3g(20mmol)、4−シクロヘキシル−1−ブロモベンゼン21.0g(88mmol)、ナトリウム tert−ブトキシド25.4g(264mmol)、キシレン混合物400mLを入れ、減圧下で脱気処理をした後、フラスコ内を窒素置換した。この混合物を約50℃まで加熱撹拌した。ここで、アリル塩化パラジウム二量体(II)(略称:(AllylPdCl)2)293mg(0.8mmol)、ジ−tert−ブチル(1−メチル−2,2−ジフェニルシクロプロピル)ホスフィン(商品名:cBRIDP(登録商標))1128mg(3.2mmol)を加え、この混合物を、6時間加熱還流させた。その後、フラスコの温度を約60℃に戻し、水約4mLを加え、析出した固体をろ別し、トルエンで洗浄した。ろ液を濃縮し、得られたキシレン溶液をシリカゲルカラムクロマトグラフィーで精製した。得られた溶液を濃縮し、濃厚なトルエン溶液を得た。このトルエン溶液をエタノールに滴下し、再沈殿した。約0℃にて析出物をろ過し、得られた固体を約75℃で減圧乾燥させ、目的物である白色固体を16.5g、収率92%で得た。また、ステップ1の合成スキームを以下に示す。
本実施例では、本発明の一態様である有機化合物、4,4’−(1,1−シクロヘキサン−ジイル)ビス{N−(4−シクロヘキシルフェニル)N−[(4´−シクロヘキシル)−1,1’−ビフェニル−4−イル]アミノベンゼン}(略称:TAPC−03)の合成方法について説明する。なお、TAPC−03の構造を以下に示す。
三口フラスコに1,1−ビス(4−アミノフェニル)シクロヘキサン5.3g(20mmol)、4−シクロヘキシル−1−ブロモベンゼン10.0g(42mmol)、ナトリウム tert−ブトキシド12.1g(126mmol)、キシレン混合物200mLを入れ、減圧下で脱気処理をした後、フラスコ内を窒素置換した。この混合物を約50℃まで加熱撹拌した。ここで、アリル塩化パラジウム二量体(II)(略称:(AllylPdCl)2)150mg(0.4mmol)、ジシクロヘキシル(2’,6’−ジメトキシ−{1,1’−ビフェニル}−2−イル)ホスフィン(略称:SPhos)660mg(1.6mmol)を加え、この混合物を、6時間加熱還流させた。その後、フラスコの温度を約60℃に戻し、水約2mLを加え、析出した固体をろ別し、トルエンで洗浄した。ろ液を濃縮し、得られたキシレン溶液をシリカゲルカラムクロマトグラフィーで精製した。得られた溶液を濃縮し、濃厚なトルエン溶液を得た。このトルエン溶液をエタノールに滴下し、再沈殿した。約0℃にて析出物をろ過し、得られた固体を約75℃で減圧乾燥させ、目的物である白色固体を9.5g、収率81%で得た。ステップ1の合成スキームを以下に示す。
三口フラスコに4,4’−(1,1−シクロヘキサン−ジイル)ビス{N−(4−シクロヘキシルフェニル)アミノベンゼン}5.8g(10mmol)、4’−シクロヘキシル−(1,1’−ビフェニル)−4−クロロベンゼン5.4g(20mmol)、ナトリウム tert−ブトキシド5.8g(60mmol)、キシレン混合物70mLを入れ、減圧下で脱気処理をした後、フラスコ内を窒素置換した。この混合物を約50℃まで加熱撹拌した。ここで、アリル塩化パラジウム二量体(II)(略称:(AllylPdCl)2)73mg(0.2mmol)、ジ−tert−ブチル(1−メチル−2,2−ジフェニルシクロプロピル)ホスフィン(略称:cBRIDP)280mg(0.8mmol)を加え、この混合物を、8時間加熱還流させた。その後、フラスコの温度を約60℃に戻し、水約2mLを加え、析出した固体をろ別し、トルエンで洗浄した。ろ液を濃縮し、得られたキシレン溶液をシリカゲルカラムクロマトグラフィーで精製した。得られた溶液を濃縮し、濃厚なトルエン溶液を得た。このトルエン溶液をエタノールに滴下し、再沈殿した。約0℃にて析出物をろ過し、得られた固体を約75℃で減圧乾燥させ、目的物である白色固体を5.8g、収率約100%で得た。また、ステップ2の合成スキームを以下に示す。
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極101を形成した。なお、その膜厚は70nmとし、電極面積は2mm×2mmとした。
比較発光素子1は発光素子1の正孔輸送層112におけるTAPC−02で形成した層を、上記構造式(vii)で表される1,1−ビス−(4−ビス(4−メチル−フェニル)−アミノ−フェニル)−シクロヘキサン(略称:TAPC)に変え、膜厚を70nmとした他は発光素子1と同様に作製した。
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極101を形成した。なお、その膜厚は70nmとし、電極面積は2mm×2mmとした。
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極101を形成した。なお、その膜厚は70nmとし、電極面積は2mm×2mmとした。
本参考合成例では、ビス{2−[6−(4−シアノ−2,6−ジメチルフェニル)−4−ピリミジニル−κN3]フェニル−κC}(2,4−ペンタンジオナト−κO,O’)イリジウム(III)(略称:[Ir(ppm−dmCP)2(acac)])の合成方法について説明する。なお、[Ir(ppm−dmCP)2(acac)]の構造を以下に示す。
4−ブロモ−3,5−ジメチルベンゾニトリル10.06g、ビス(ピナコラート)ジボロン18.35g、酢酸カリウム21.73g、ジメチルスルホキシド240mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。フラスコ内を減圧下で撹拌することで脱気した後、[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)ジクロリドジクロロメタン付加物(略称:Pd(dppf)Cl2・CH2Cl2)0.59g、2−ジシクロヘキシルホスフィノ−2’,6’−ジメトキシビフェニル(略称:S−Phos)0.59gを加え、100℃で32時間半撹拌した。所定時間経過後、トルエンによる抽出を行った。その後、ヘキサン:酢酸エチル=10:1を展開溶媒とするシリカゲルカラムクロマトグラフィーで精製し、目的物を得た(白色固体、収量5.89g、収率48%)。ステップ1の合成スキームを下記式(a−1)に示す。
次に、4−クロロ−6−フェニルピリミジン0.74g、上記ステップ1で得られた、3,5−ジメチル−4−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)ベンゾニトリル1.28g、リン酸三カリウム3.23g、トルエン43mL、水4.3mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。フラスコ内を減圧下で撹拌して脱気した後、トリス(ジベンジリデンアセトン)ジパラジウム(0)(略称:Pd2(dba)3)0.094g、トリス(2,6−ジメトキシフェニル)ホスフィン(略称:P(2,6−MeOPh)3)0.19gを加え、110℃で23時間撹拌した。所定時間経過後、トルエンによる抽出を行った。その後、ヘキサン:酢酸エチル=5:1を展開溶媒とするシリカゲルカラムクロマトグラフィーで精製し、目的のピリミジン誘導体、Hppm−dmCPを得た(白色固体、収量0.97g、収率88%)。ステップ2の合成スキームを下記式(a−2)に示す。
次に、2−エトキシエタノール15mLと水5mL、上記ステップ2で得たHppm−dmCP1.60g、塩化イリジウム水和物(IrCl3・H2O)(フルヤ金属社製)0.81gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を3時間照射し、反応させた。所定時間経過後、得られた残差をメタノールで吸引ろ過、洗浄し、複核錯体[Ir(ppm−dmCP)2Cl]2を得た(橙色固体、収量1.45g、収率67%)。ステップ3の合成スキームを下記式(a−3)に示す。
2−エトキシエタノール20mL、上記ステップ3で得た複核錯体、[Ir(ppm−dmCP)2Cl]2 1.44g、アセチルアセトン(略称:Hacac)0.41g、炭酸ナトリウム0.93gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を4時間照射した。得られた残差を、ジクロロメタンで吸引ろ過した後、ろ液を濃縮した。得られた固体を、ヘキサン:酢酸エチル=2:1を展開溶媒とするシリカゲルカラムクロマトグラフィーにより精製した後、ジクロロメタンとメタノールの混合溶媒にて再結晶することにより、有機金属錯体、[Ir(ppm−dmCP)2(acac)]を黄橙色粉末として得た(収量0.19g、収率7%)。得られた黄橙色粉末0.19gを、トレインサブリメーション法により昇華精製した。昇華精製条件は、圧力2.7Pa、アルゴンガスを流量11mL/minで流しながら、355℃で固体を加熱した。昇華精製後、目的物の黄橙色固体を収量0.092g、収率48%で得た。ステップ4の合成スキームを下記式(a−4)に示す。
Claims (22)
- 請求項1において、前記Ar1およびAr4が置換または無置換のフェニレン基である有機化合物。
- 請求項1または請求項2において、前記Ar2およびAr3が置換または無置換のビフェニルジイル基である有機化合物。
- 請求項1において、前記Ar1乃至Ar4が置換または無置換のフェニレン基である有機化合物。
- 請求項1乃至請求項7のいずれか一項において、
m、n、pおよびsはそれぞれ独立に1乃至3の整数を表す有機化合物。 - 請求項1乃至請求項8のいずれか一項において、
前記m、n、pおよびsが1である有機化合物。 - 請求項1乃至請求項5のいずれか一項において、
前記R1乃至R4がそれぞれ独立にシクロヘキシル基である有機化合物。 - 第1の電極と、
第2の電極と、
前記第1の電極および前記第2の電極の間に位置するEL層と、を有し、
前記EL層が、請求項1乃至請求項14のいずれか一項に記載の有機化合物を含む発光素子。 - 第1の電極と、
第2の電極と、
前記第1の電極および前記第2の電極の間に位置するEL層と、を有し、
前記EL層は、少なくとも発光層と正孔輸送層とを有し、
前記正孔輸送層が、請求項1乃至請求項14のいずれか一項に記載の有機化合物を含む発光素子。 - 第1の電極と、
第2の電極と、
前記第1の電極および前記第2の電極の間に位置するEL層と、を有し、
前記EL層は、少なくとも発光層と正孔注入層とを有し、
前記正孔注入層が、請求項1乃至請求項14のいずれか一項に記載の有機化合物を含む発光素子。 - 第1の電極と、
第2の電極と、
前記第1の電極および前記第2の電極の間に位置するEL層と、を有し、
前記EL層は、発光層、正孔輸送層および正孔注入層を有し、
前記正孔輸送層および前記正孔注入層に、請求項1乃至請求項14のいずれか一項に記載の有機化合物を含む発光素子。 - 請求項15乃至請求項18に記載の発光素子と、トランジスタ、または、基板と、を有する発光装置。
- 請求項19に記載の発光装置と、センサ、操作ボタン、スピーカ、または、マイクと、
を有する電子機器。 - 請求項19に記載の発光装置と、筐体と、を有する照明装置。
- 請求項1乃至請求項14のいずれか一項に記載の有機化合物を含む電子デバイス。
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US20220204438A1 (en) | 2022-06-30 |
CN112154135A (zh) | 2020-12-29 |
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