JP6024455B2 - 発光素子材料および発光素子 - Google Patents
発光素子材料および発光素子 Download PDFInfo
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- JP6024455B2 JP6024455B2 JP2012523538A JP2012523538A JP6024455B2 JP 6024455 B2 JP6024455 B2 JP 6024455B2 JP 2012523538 A JP2012523538 A JP 2012523538A JP 2012523538 A JP2012523538 A JP 2012523538A JP 6024455 B2 JP6024455 B2 JP 6024455B2
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- 239000000463 material Substances 0.000 title claims description 112
- 239000010410 layer Substances 0.000 claims description 104
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 84
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- -1 acridyl group Chemical group 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 30
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
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- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YPJRZWDWVBNDIW-UHFFFAOYSA-N n,n-diphenyl-4-[2-[4-[4-[2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1C(C=C1)=CC=C1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPJRZWDWVBNDIW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MHJUNMARMFAUBI-UHFFFAOYSA-N n-phenyliminobenzamide Chemical compound C=1C=CC=CC=1C(=O)N=NC1=CC=CC=C1 MHJUNMARMFAUBI-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 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
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 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
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 150000004322 quinolinols Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 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
- 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
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 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
- 239000010703 silicon Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 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
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 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
- 150000003852 triazoles Chemical class 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
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C07D401/02—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 two hetero rings
- C07D401/10—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 two hetero rings linked by a carbon chain containing aromatic rings
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Description
化合物[1]の合成
2−ブロモフルオレン25.0g、ヨウ素12.2gおよび酢酸680mlからなる溶液に、窒素気流下で、硫酸68mLをゆっくり加えた。この混合溶液に亜硝酸ナトリウム7.1gをゆっくり加えた後、還流下で2時間撹拌した。反応混合物を室温に冷ました後、析出物をろ過した。得られた析出物を、酢酸エチル、水およびメタノールでそれぞれ洗浄し、真空乾燥することにより、2−ブロモ−7−ヨードフルオレン25.9g(収率68%)を得た。
化合物[1]: 1H−NMR (CDCl3 (d=ppm)) δ 1.60 (s,6H),7.29 (td,2H),7.37−7.58 (m,6H),7.63−7.78 (m,7H),7.81−7.89 (m,6H),7.94 (dt,1H),8.18 (d,2H),8.62 (dd,1H),8.93 (d,1H)。
化合物[2]の合成
中間体(A)2.4g、4−(4−ピリジル)フェニルボロン酸ピナコールエステル2.1g、ジメトキシエタン24mLおよび1.5M炭酸ナトリウム水溶液7mLの混合溶液を窒素置換した後、ビス(トリフェニルホスフィン)パラジウムジクロリド33mgを加え、還流下で12時間半加熱撹拌した。反応混合物を室温に冷却した後、水24mLを加え、析出物をろ過し、真空乾燥した。析出物をシリカゲルカラムクロマトグラフィーにより精製し、溶出液に、スカベンジャーとしてQuadraSil(登録商標)0.5gを加え、室温で1時間撹拌した後、シリカパッドでろ過し、溶媒を留去した。o−キシレン73mLを用いて得られた固体の再結晶をおこない、白色結晶2.2g(収率73%)を得た。
化合物[2]: 1H−NMR (CDCl3 (d=ppm)) δ 1.60 (s,6H),7.31 (td,2H),7.41−7.52 (m,4H),7.55−7.59 (m,3H),7.64−7.89 (m,13H),8.18 (d,2H),8.69 (dd,2H)。
化合物[3]の合成
2−ブロモ−7−ヨード−9,9−ジメチルフルオレン11.5g、4−(9−カルバゾリル)フェニルボロン酸9.1g、ジメトキシエタン144mLおよび1.5M炭酸ナトリウム水溶液42mLの混合溶液を窒素置換した後、ビス(トリフェニルホスフィン)パラジウムジクロリド202mgを加え、60℃で5.5時間加熱撹拌した。反応混合物を約40℃に冷却した後、水200mLを加え、析出物をろ過した。析出物をメタノールで洗浄し、ろ過し、真空乾燥した。析出物をシリカゲルカラムクロマトグラフィーにより精製し、溶出液をエバポレートした。得られた固体に、メタノール100mlを加え、ろ過し、真空乾燥することにより、中間体(C)10.1g(収率68%)を得た。
化合物[3]: 1H−NMR (CDCl3 (d=ppm)) δ 1.65 (s,6H),7.30 (td,2H),7.38−7.52 (m,5H),7.64−7.98 (m,15H),8.18 (d,2H),8.63 (dd,1H),8.94 (d,1H)。
化合物[4]の合成
中間体(C) 5.1g、4−(2−ピリジル)フェニルボロン酸2.2g、ジメトキシエタン49mLおよび1.5M炭酸ナトリウム水溶液14mLの混合溶液を窒素置換した後、ビス(トリフェニルホスフィン)パラジウムジクロリド69mgを加え、還流下で4時間半加熱撹拌した。反応混合物を室温に冷却した後、水49mLを加え、析出物をろ過し、真空乾燥した。析出物をシリカゲルカラムクロマトグラフィーにより精製し、溶出液にQuadraSil(登録商標)0.8gを加え、室温で1時間撹拌した後、セライトでろ過した。ろ液をエバポレートした後、得られた固体にメタノール20mlを加え、ろ過した。ろ液を真空乾燥した後、N,N−ジメチルホルムアミド54mLを用いて再結晶をおこなった。さらに、N,N−ジメチルホルムアミド46mLを用いて再結晶をおこなうことで、白色結晶3.5g(収率60%)を得た。
化合物[4]: 1H−NMR (CDCl3 (d=ppm)) δ 1.65 (s,6H),7.31 (td,2H),7.41−7.52 (m,4H),7.66−7.93 (m,15H),8.12−8.19 (m,4H),8.74 (dt,1H)。
ITO透明導電膜を150nm堆積させたガラス基板(ジオマテック(株)製、表面電気抵抗11Ω/□、スパッタ品)を38×46mmに切断した後、エッチングを行い、ITO透明導電膜を所定の電極形状に形成した。得られた基板を“セミコクリーン56”(商品名、フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。この基板を、素子を作製する直前に1時間UV−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10−4Pa以下になるまで排気した。ITO透明導電膜上に、抵抗加熱法によって、まず正孔注入層として、銅フタロシアニンを10nmの厚さ、正孔輸送層として、4,4’−ビス(N−(1−ナフチル)−N−フェニルアミノ)ビフェニルを50nmの厚さ、それぞれ蒸着した。次に、発光層として、ホスト材料である化合物(H−1)およびドーパント材料である化合物(D−1)を混合した層を、ドーパント濃度が5重量%になるようにして40nmの厚さに蒸着した。次に、電子輸送層として化合物[1]とドナー性化合物であるフッ化リチウムを混合した層を、蒸着速度比1:1(0.05nm/s:0.05nm/s)で20nmの厚さに蒸着して積層した。
ホスト材料、ドーパント材料および電子輸送層として表1および表2に記載した材料を用いた以外は、実施例1と同様にして発光素子を作製した。結果は表1および表2に示した。なお、化合物[5]〜[19]、2E−1は下記に示す化合物である。
ホスト材料、ドーパント材料および電子輸送層として表2に記載した材料を用いた以外は、実施例1と同様にして発光素子を作製した。結果は表2に示した。なお、表1および表2中、化合物E−1、E−2、E−3、E−4は下記に示す化合物である。
ホスト材料、ドーパント材料および電子輸送層として表3に記載した材料を用いた以外は、実施例1と同様にして発光素子を作製した。評価結果は表3に示した。なお、表3中、化合物H−2〜H−8、D−2〜D−10は下記に示す化合物である。
ホスト材料およびドーパント材料として表4に記載した材料および電子輸送層としてトリス(8−キノリノラート)アルミニウム(Alq)を用いた以外は、実施例1と同様にして発光素子を作製した。評価結果は表4に示した。
Claims (12)
- 下記一般式(1)で表される化合物を含有する発光素子材料:
- 電子受容性窒素を含む芳香族複素環基がピリジル基、キノリニル基、イソキノリニル基、キノキサニル基、ピラジニル基、ピリミジル基、ピリダジニル基、フェナントロリニル基、イミダゾピリジル基、トリアジル基、アクリジル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、ビピリジル基およびターピリジル基からなる群より選ばれる請求項1記載の発光素子材料。
- 一般式(2)におけるR7がL1との連結に用いられる請求項1〜3のいずれか記載の発光素子材料。
- 一般式(2)におけるR2がL2との連結に用いられる請求項1〜4のいずれか記載の発光素子材料。
- 一般式(3)におけるR15、R18またはR21がL1との連結に用いられる請求項1〜5のいずれか記載の発光素子材料。
- 陽極と陰極の間に有機層が存在し、電気エネルギーにより発光する発光素子であって、前記有機層に請求項1〜6のいずれか記載の発光素子材料を含有する発光素子。
- 前記有機層が電子輸送層を含み、電子輸送層が請求項1〜6のいずれか記載の発光素子材料を含む請求項7記載の発光素子。
- 前記電子輸送層がさらにドナー性化合物を含む請求項8記載の発光素子。
- 前記ドナー性化合物がアルカリ金属、アルカリ金属を含有する無機塩、アルカリ金属と有機物との錯体、アルカリ土類金属、アルカリ土類金属を含有する無機塩またはアルカリ土類金属と有機物との錯体である請求項9記載の発光素子。
- 前記ドナー性化合物がアルカリ金属と有機物との錯体またはアルカリ土類金属と有機物との錯体である請求項10記載の発光素子。
- 前記有機層が発光層を含み、発光層が請求項1〜6のいずれか記載の発光素子材料を含む請求項7記載の発光素子。
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