JP6617706B2 - 芳香族アミン化合物、発光素子材料および発光素子 - Google Patents
芳香族アミン化合物、発光素子材料および発光素子 Download PDFInfo
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- JP6617706B2 JP6617706B2 JP2016542131A JP2016542131A JP6617706B2 JP 6617706 B2 JP6617706 B2 JP 6617706B2 JP 2016542131 A JP2016542131 A JP 2016542131A JP 2016542131 A JP2016542131 A JP 2016542131A JP 6617706 B2 JP6617706 B2 JP 6617706B2
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- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical group N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 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
- 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
- 238000005464 sample preparation method 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 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
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 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
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
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- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Plural Heterocyclic Compounds (AREA)
Description
ここで、Rは、水素や、重水素や、置換され得るアルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アルキルアミノ基またはシリル基から選ばれ得る1種または複数種であり;
L1、L2は同じであるかまたは異なっていてもよく、アリーレン基またはヘテロアリーレン基からそれぞれ選ばれ;
Ar1、Ar2は同じであるかまたは異なっていてもよく、アリール基またはヘテロアリール基からそれぞれ選ばれ;
Ar3、Ar4は、同じであるかまたは異なっているヘテロアリール基であってよく;
ここで、R1〜R2は同じであるかまたは異なっていてもよく、水素や、重水素や、ハロゲンや、置換され得るアルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、シアノ基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アルキルアミノ基またはシリル基からそれぞれ選ばれ得る1種または複数種であり、隣接する置換基と結合して環を形成してもよい。
ここでRは、水素や、重水素や、置換され得るアルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アルキルアミノ基またはシリル基から選ばれ得る1種または複数種であり;
L1、L2は同じであるかまたは異なっていてもよく、アリーレン基またはヘテロアリーレン基からそれぞれ選ばれ;
Ar1、Ar2は同じであるかまたは異なっていてもよく、アリール基またはヘテロアリール基からそれぞれ選ばれ;
Ar3、Ar4は、同じであるかまたは異なっているヘテロアリール基であってよく;
ここで、R1〜R2は同じであるかまたは異なっていてもよく、水素や、重水素や、ハロゲンや、置換され得るアルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、シアノ基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アルキルアミノ基またはシリル基からそれぞれ選ばれ得る1種または複数種であり、隣接する置換基と結合して環を形成してもよい。合成の簡単さとコストの角度から考えると、好ましくは、L1とL2はアリーレン基である。
ここで、Rは、水素や、重水素や、置換され得るアルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アルキルアミノ基またはシリル基から選ばれ得る1種または複数種であり;
L1、L2は同じであるかまたは異なっていてもよく、アリーレン基またはヘテロアリーレン基からそれぞれ選ばれ;
Ar1、Ar2は同じであるかまたは異なっていてもよく、アリール基またはヘテロアリール基からそれぞれ選ばれ;
Ar3、Ar4は、同じであるかまたは異なっているヘテロアリール基であってよく;
ここで、R1〜R2は同じであるかまたは異なっていてもよく、水素や、重水素や、ハロゲンや、置換され得るアルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、シアノ基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アルキルアミノ基またはシリル基からそれぞれ選ばれ得る1種または複数種であり、隣接する置換基と結合して環を形成してもよい。
化合物[2](2,5−ビス(4−(N−フェニル)−(N−3−ピリジル)アミノフェニル)チオフェン)、
化合物[5](2,5−ビス(4−(N−4−ビフェニル)−(N−3−ピリジル)アミノフェニル)チオフェン)、
化合物[6](2,5−ビス(4−(N−4−ビフェニル)−(N−4−ピリジル)アミノフェニル)チオフェン)、
化合物[8](2,5−ビス(4−(N−3−ビフェニル)−(N−3−ピリジル)アミノフェニル)チオフェン)、
化合物[87](1−メチル−2,5−ビス(4−(N−4−ビフェニル)−(N−3−ピリジル)アミノフェニル)−1H−ピロール)、
化合物[31](2,5−ビス(4−(N−1−ナフチル)−(N−4−ピリジルアミノ)フェニル)チオフェン)、
化合物[32](2,5−ビス(4−(N−3−ビフェニル)−(N−4−ピリジルアミノ)フェニル)チオフェン)、
化合物[134](2,5−ビス(4−(N−3−(3’−メチル)ビフェニル)−(N−4−ピリジルアミノ)フェニル)チオフェン)、
化合物[11](2,5−ビス(4−(N−4−(3−ピリジル)フェニル)−(N−3−ピリジルアミノ)フェニル)チオフェン)、
化合物[12](2,5−ビス(4−(N−4−(3−ピリジル)フェニル)−(N−4−ピリジルアミノ)フェニル)チオフェン)、
化合物[13](2,5−ビス(4−(N−4−(4−ピリジル)フェニル)−(N−2−ピリジルアミノ)フェニル)チオフェン)、
化合物[14](2,5−ビス(4−(N−4−(4−ピリジル)フェニル)−(N−3−ピリジルアミノ)フェニル)チオフェン)、
化合物[15](2,5−ビス(4−(N−4−(4−ピリジル)フェニル)−(N−4−ピリジルアミノ)フェニル)チオフェン)、
化合物[18](2,5−ビス(4−(N−3−(3−ピリジル)フェニル)−(N−4−ピリジルアミノ)フェニル)チオフェン)、
化合物[21](2,5−ビス(4−(N−3−(4−ピリジル)フェニル)−(N−4−ピリジルアミノ)フェニル)チオフェン)、
化合物[140](2,5−ビス(4−(N−4−ビフェニル)−(N−3−キノリルアミノ)フェニル)チオフェン)、
化合物[142](2,5−ビス(4−(N−4−ビフェニル)−(N−6−キノリルアミノ)フェニル)チオフェン)、
化合物[143](2,5−ビス(4−(N−4−ビフェニル)−(N−2−ピリミジニルアミノ)フェニル)チオフェン)、
化合物[144](2,5−ビス(4−(N−4−ビフェニル)−(N−5−ピリミジニルアミノ)フェニル)チオフェン)、
化合物[147](2,5−ビス(4−(N−4−ビフェニル)−(N−4−フェニルアミノ)フェニル)チオフェン)、
化合物[148](2,5−ビス(4−(N−4−ビフェニル)−(N−1−ナフチルアルキニルアミノ)フェニル)チオフェン)、
化合物[149](2,5−ビス(4−(N−4−ビフェニル)−(N−2−ナフチルアルキニルアミノ)フェニル)チオフェン)、
NPD (N,N’−ジフェニル−N,N’−ビス(1−ナフチル)−1,1’−ビフェニル−4,4’−ジアミン)、
F4−TCNQ (2,3,5,6−テトラフルオロ−7,7’,8,8’−テトラシアノキノジメタン)、
BH (9−(2−ナフチル)−10−(4−(1−ナフチル)フェニル)アントラセン)、
BD (E−7−(4−(ジフェニルアミノ)スチリル)−N,N−ジフェニル−9,9’−ジメチルフルオレン−2−アミン)、
Alq3 (トリス(8−キノリナート)アルミニウム)
TBDB (N,N,N’,N’−4(4−ビフェニル)ジアミノビフェニル)。
化合物[2]の合成
窒素ガス雰囲気下で、2,5−ジブロモチオフェン24.2g(100mmol)、4−クロロフェニルボロン酸34.4g(220mmol)、テトラキス(トリフェニルホスフィン)パラジウム5.7g(5.0mmol)、1.5M炭酸ナトリウム水溶液200ml(300mmol)、およびジメチルエーテル100ml(DME)を反応器に加え、110℃で加熱して一晩撹拌する。室温まで冷却し、濾過し、濾過液は有機層と水層に分層し、有機層は減圧濃縮される。得られた固体をエタノールで洗浄し、21.3gの2,5−ビス(4−クロロフェニル)チオフェンを得る。
HPLC(純度=97.1%)。
化合物[5]の合成
N−フェニル−3−ピリジルアミンの代わりにN−(4−ビフェニル)−3−ピリジルアミンを使用する以外は、実施例1と同じである。1.1gの化合物[5](淡黄色の固体)を得る。
HPLC(純度=98.1%)。
化合物[6]の合成
N−フェニル−4−ピリジルアミンの代わりにN−(4−ビフェニル)−3−ピリジルアミンを使用する以外は、実施例1と同じである。2.2gの化合物[6](淡黄色の固体)を得る。
HPLC(純度=99.02%)。
化合物[8]の合成
N−フェニル−3−ピリジルアミンの代わりにN−(3−ビフェニル)−3−ピリジルアミンを使用する以外は、実施例1と同じである。1.5gの化合物[8](淡黄色の固体)を得る。
HPLC(純度=97.8%)。
化合物[31]の合成
N−ナフチル−3−ピリジルアミンの代わりにN−(3−ビフェニル)−3−ピリジルアミンを使用する以外は、実施例1と同じである。2.5gの化合物[31](淡黄色の固体)を得る。
HPLC(純度=97.2%)。
化合物[32]の合成
N−ビフェニル−3−ピリジルアミンの代わりにN−(3−ビフェニル)−3−ピリジルアミンを使用する以外は、実施例1と同じである。3.2gの化合物[32](淡黄色の固体)を得る。
HPLC(純度=95.0%)。
化合物[134]の合成
N−3−(3’−メチルビフェニル)−4−ピリジルアミンの代わりにN−フェニル−3−ピリジルアミンを使用する以外は、実施例1と同じである。3.6gの化合物[134](淡黄色の固体)を得る。
HPLC(純度=95.9%)。
化合物[87]の合成
窒素ガス雰囲気下で、N−メチルピロール3.24g(40mmol)、4−クロロブロモベンゼン22.9g(120mmol)、ビス(ジフェニルホスフィノ)プロパン−パラジウムクロリド243mg(0.39mmol)、炭酸カリウム15.68g(160mmol)、ジメチルアセトアミド150ml(DMAC)を反応器に加え、110℃で加熱して一晩撹拌する。室温まで冷却し、濾過し、濾過液は減圧濃縮される。得られた固体をエタノールで洗浄し、4.3gの2,5−ビス(4−クロロフェニル)−1−メチルピロールを得る。
窒素ガス雰囲気下で、2,5−ビス(4−クロロフェニル)−1−メチルピロール1.50g(4.96mmol)、N−(4−ビフェニル)−3−ピリジルアミン3.50g(14.2mmol)、ビス(ジベンジリデンアセトン)パラジウム30mg(0.052mmol)、テトラフルオロほう酸トリ−tert−ブチルホスフィン30mg(0.10mmol)、ナトリウムt−ブトキシド2.80g(29.1mmol)、および1,2−ジメチルベンゼン60mlを反応器に加え、110℃で加熱して一晩撹拌する。室温まで冷却し、濾過し、濾過液は減圧濃縮される。得られた固体をエタノールで洗浄した後、シリカゲルカラム(溶出液:ジクロロメタン/酢酸エチル=4/1)で精製し、2.4gの粗生成物を得る。粗生成物を圧力2×10−3Pa、温度320℃下で昇華させて1.0gの化合物[87](淡黄色の固体)を得る。
HPLC(純度=97.8%)。
薄膜サンプルの作製方法
無アルカリガラス基板(旭硝子株式会社、AN100)に20分間のUVオゾン洗浄処理を行い、さらに真空蒸着装置内に設置し、装置内の真空度が1×10−3Paよりも高い真空度の条件まで排気を行い、抵抗加熱蒸着法によって、化合物[2]を蒸着して約50nmの薄膜を調製する。蒸着速度は0.1nm/sである。
実施例10
化合物[5]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[6]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[8]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[87]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[11]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[12]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[13]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[14]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[15]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[18]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[21]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[140]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[142]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[143]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
化合物[144]で化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
NPDで化合物[2]を代替する以外は、実施例9と同じである。
有機発光素子を評価する。評価結果については表2参照。
実施例25
無アルカリガラスは、イソプロピルアルコールの中で15分間超音波洗浄した後、大気中で30分間のUVオゾン洗浄処理を行う。真空蒸着法を利用し、まず、アルミニウム100nmを蒸着して陽極を作成し、続いて、陽極上に正孔注入層(NPDとF4−TCNQ(重量比97:3)、50nm)、正孔輸送層(NPD、80nm)、青色発光層(BHとBD(重量比97:3、20nm)、電子輸送層(Alq3、30nm)、電子注入層(LiF、1nm)を順次積層蒸着した後、MgとAg(重量比10:1、15nm)を共に蒸着して半透明の陰極を作成する。
被覆層材料が化合物[6]である以外は、実施例25と同じ素子になるように作製して評価を行う。評価結果については表3参照。
被覆層材料が化合物[8]である以外は、実施例25と同じ素子になるように作製して評価を行う。評価結果については表3参照。
被覆層材料がNPDである以外は、実施例25と同じ素子になるように作製して評価を行う。評価結果については表3参照。
被覆層材料がTBDBである以外は、実施例25と同じ素子になるように作製して評価を行う。評価結果については表3参照。
Claims (2)
- 下記一般式(1)に示す化合物を含有することを特徴とする、有機発光素子において発光層の光を透過させる上部電極を被覆する被覆層材料:
L1、L2は同じであるかまたは異なり、フェニレン基、ナフチレン基、ビフェニレン基、フェナントリレン基、ターフェニレン基またはピレニレン基であり;
Ar1、Ar2は同じであるかまたは異なり、アリール基であり;
Ar3、Ar4は同じであるかまたは異なり、隣接する原子に二重結合で連結する窒素原子を有するヘテロアリール基であり;
ここで、R1、R2は水素である。 - 基板と、第1電極と、発光層を含む1層以上の有機層膜と、前記発光層の光を透過させる第2電極とを備え、前記第2電極を被覆する被覆層をさらに有し;前記被覆層が、請求項1に記載の被覆層材料を含有することを特徴とする有機発光素子。
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