JP2021091726A - 有機化合物 - Google Patents
有機化合物 Download PDFInfo
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- JP2021091726A JP2021091726A JP2021035121A JP2021035121A JP2021091726A JP 2021091726 A JP2021091726 A JP 2021091726A JP 2021035121 A JP2021035121 A JP 2021035121A JP 2021035121 A JP2021035121 A JP 2021035121A JP 2021091726 A JP2021091726 A JP 2021091726A
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- JP
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- Prior art keywords
- light emitting
- layer
- hole transport
- abbreviation
- emitting element
- Prior art date
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- 150000002894 organic compounds Chemical class 0.000 title claims description 70
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 46
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 44
- 125000004429 atom Chemical group 0.000 claims description 27
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 150000001721 carbon Chemical class 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 310
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 125
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- 239000007924 injection Substances 0.000 abstract description 53
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- 238000000034 method Methods 0.000 description 57
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- 229910052757 nitrogen Inorganic materials 0.000 description 50
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- 125000001072 heteroaryl group Chemical group 0.000 description 10
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 9
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 7
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 238000005192 partition Methods 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- 239000011701 zinc Substances 0.000 description 7
- HEZMWWAKWCSUCB-PHDIDXHHSA-N (3R,4R)-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylic acid Chemical compound O[C@@H]1C=CC(C(O)=O)=C[C@H]1O HEZMWWAKWCSUCB-PHDIDXHHSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229910008449 SnF 2 Inorganic materials 0.000 description 6
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 6
- 125000005595 acetylacetonate group Chemical group 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 6
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- 238000004364 calculation method Methods 0.000 description 6
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- 238000004809 thin layer chromatography Methods 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
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- 238000001514 detection method Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 4
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical group C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 4
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
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- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- VDHOGVHFPFGPIP-UHFFFAOYSA-N 9-[3-[5-(3-carbazol-9-ylphenyl)pyridin-3-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=NC=C(C=2)C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 VDHOGVHFPFGPIP-UHFFFAOYSA-N 0.000 description 2
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Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- C—CHEMISTRY; METALLURGY
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- H05B45/60—Circuit arrangements for operating LEDs comprising organic material, e.g. for operating organic light-emitting diodes [OLED] or polymer light-emitting diodes [PLED]
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- H05B47/00—Circuit arrangements for operating light sources in general, i.e. where the type of light source is not relevant
- H05B47/10—Controlling the light source
- H05B47/105—Controlling the light source in response to determined parameters
- H05B47/11—Controlling the light source in response to determined parameters by determining the brightness or colour temperature of ambient light
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- 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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Abstract
Description
を有する発光装置である。
図1(A)は本発明の一態様の発光素子を表す図である。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、EL層103は第1の電極101側から正孔注入層111、第1の正孔輸送層112−1、第2の正孔輸送層112−2、第3の正孔輸送層112−3及び発光層113を有している。また、電子輸送層114、電子注入層115を有していても良い。
これら導電性材料は、真空蒸着法やスパッタリング法などの乾式法、インクジェット法、スピンコート法等を用いて成膜することが可能である。また、ゾル−ゲル法を用いて湿式法で形成しても良いし、金属材料のペーストを用いて湿式法で形成してもよい。
本実施の形態では、本発明の一態様の有機化合物について説明する。
本実施の形態では、実施の形態1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1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1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1に記載の発光素子は寿命が良好であり、信頼性の良好な発光素子である。その結果、本実施の形態に記載の電子機器は、信頼性の良好な発光部を有する電子機器とすることが可能である。
本合成例では、下記構造式(101)で表されるN−[3−(ジベンゾチオフェン−4−イル)フェニル]−N−フェニル−4−ビフェニルアミン(略称:mThBA1BP−II)の合成法について説明する。
反応後、この反応混合液にトルエン250mLを加え、フロリジール、セライトを通してろ過した。得られたろ液を濃縮し、シリカゲルカラムクロマトグラフィー(展開溶媒 トルエン:ヘキサン=1:4)による精製を行った。得られたフラクションを濃縮し、アセトンとメタノールを加えて超音波をかけた後、再結晶したところ、白色粉末を収量1.6g、収率64%で得た。上記反応スキームを下に示す。
1H NMR(CDCl3,300MHz):δ(ppm)=7.09(1H, t, J=7.5Hz), 7.23−7.66(21H, m), 7.83−7.86(1H, m), 8.13(1H, dd, J=1.5Hz, 7.8Hz), 8.17−8.20(1H, m)。
本合成例では、下記構造式(100)で表されるN−[4−(ジベンゾチオフェン−4−イル)フェニル]−N−フェニル−4−ビフェニルアミン(略称:ThBA1BP−II)の合成法について説明する。
1H NMR(CDCl3,300MHz):δ(ppm)=7.06(1H, t, J=7.2Hz), 7.17(21H, m), 7.80−7.83(1H, m), 8.10−8.17(2H, m)。
本合成例では、下記構造式で表されるN,N−ビス[4−(ジベンゾチオフェン−4−イル)フェニル]−4−ビフェニルアミン(略称:ThBB1BP−II)の合成法について説明する。
反応後、この反応混合液にトルエン250mLを加え、フロリジール、セライトを通してろ過した。得られたろ液を濃縮し、シリカゲルカラムクロマトグラフィー(展開溶媒 トルエン:ヘキサン=1:4)による精製を行った。目的物の白色粉末を収量1.8g、収率90%で得た。反応スキームを下に示す。
1H NMR(CDCl3,300MHz):δ(ppm)=7.33−7.64(21H, m), 7.71(4H, d, J=6.3Hz), 7.84−7.87(2H, m), 8.14(2H, dd, J=2.1Hz, 7.8Hz), 8.17−8.20(2H, m)。
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110nm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における第1の正孔輸送層112−1を膜厚25nmで形成し、第2の正孔輸送層112−2を形成しない他は発光素子1と同様に作製した。すなわち、比較発光素子1は、第2の正孔輸送層112−2を形成せず、その分の膜厚を第1の正孔輸送層112−1に積み増した発光素子ということができる。
比較発光素子2は、発光素子1における第1の正孔輸送層112−1を膜厚30nmで形成し、第2の正孔輸送層112−2及び第3の正孔輸送層112−3を形成しない他は、発光素子1と同様に作製した。すなわち、比較発光素子2は、第2の正孔輸送層112−2及び第3の正孔輸送層112−3を形成せず、その分の膜厚を第1の正孔輸送層112−1に積み増した発光素子ということができる。
比較発光素子3は、発光素子1における第1の正孔輸送層112−1を膜厚25nmで形成し、第3の正孔輸送層112−3を形成しない他は、発光素子1と同様に作製した。すなわち、比較発光素子3は第3の正孔輸送層112−3を形成せず、その分の膜厚を第1の正孔輸送層112−1に積み増した発光素子ということができる。
2 制御部
3 センサ部
4 照明部
5 データベース
6 発光装置部
101 第1の電極
102 第2の電極
103 EL層
111 正孔注入層
112−1 第1の正孔輸送層
112−2 第2の正孔輸送層
112−3 第3の正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
116 電荷発生層
117 P型層
118 電子リレー層
119 電子注入バッファ層
400 基板
401 第1の電極
403 EL層
404 第2の電極
405 シール材
406 シール材
407 封止基板
412 パッド
420 ICチップ
501 第1の電極
502 第2の電極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 駆動回路部(ソース線駆動回路)
602 画素部
603 駆動回路部(ゲート線駆動回路)
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用FET
612 電流制御用FET
613 第1の電極
614 絶縁物
616 EL層
617 第2の電極
618 発光素子
730 絶縁膜
770 平坦化絶縁膜
772 導電膜
782 発光素子
783 液滴吐出装置
784 液滴
785 層
786 EL層
788 導電膜
901 筐体
902 液晶層
903 バックライトユニット
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 EL層
956 電極
1001 基板
1002 下地絶縁膜
1003 ゲート絶縁膜
1006 ゲート電極
1007 ゲート電極
1008 ゲート電極
1020 第1の層間絶縁膜
1021 第2の層間絶縁膜
1022 電極
1024W 第1の電極
1024R 第1の電極
1024G 第1の電極
1024B 第1の電極
1025 隔壁
1028 EL層
1029 第2の電極
1031 封止基板
1032 シール材
1033 透明な基材
1034R 赤色の着色層
1034G 緑色の着色層
1034B 青色の着色層
1035 ブラックマトリクス
1036 オーバーコート層
1037 第3の層間絶縁膜
1040 画素部
1041 駆動回路部
1042 周辺部
1400 液滴吐出装置
1402 基板
1403 液滴吐出手段
1404 撮像手段
1405 ヘッド
1406 点線
1407 制御手段
1408 記憶媒体
1409 画像処理手段
1410 コンピュータ
1411 マーカー
1412 ヘッド
1413 材料供給源
1414 材料供給源
1415 材料供給源
1416 ヘッド
2001 筐体
2002 光源
3001 照明装置
5000 表示領域
5001 表示領域
5002 表示領域
5003 表示領域
5004 表示領域
5005 表示領域
7101 筐体
7103 表示部
7105 スタンド
7107 表示部
7109 操作キー
7110 リモコン操作機
7201 本体
7202 筐体
7203 表示部
7204 キーボード
7205 外部接続ポート
7206 ポインティングデバイス
7210 第2の表示部
7301 筐体
7302 筐体
7303 連結部
7304 表示部
7305 表示部
7306 スピーカ部
7307 記録媒体挿入部
7308 LEDランプ
7309 操作キー
7310 接続端子
7311 センサ
7401 筐体
7402 表示部
7403 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
7400 携帯電話機
9033 留め具
9034 スイッチ
9035 電源スイッチ
9036 スイッチ
9038 操作スイッチ
9310 携帯情報端末
9311 表示パネル
9312 表示領域
9313 ヒンジ
9315 筐体
9630 筐体
9631 表示部
9631a 表示部
9631b 表示部
9632a タッチパネル領域
9632b タッチパネル領域
9633 太陽電池
9634 充放電制御回路
9635 バッテリー
9636 DCDCコンバータ
9637 操作キー
9638 コンバータ
9639 ボタン
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CN108369996B (zh) | 2021-07-09 |
KR20180095872A (ko) | 2018-08-28 |
US10930855B2 (en) | 2021-02-23 |
JP6850261B2 (ja) | 2021-03-31 |
CN113773298A (zh) | 2021-12-10 |
CN108369996A (zh) | 2018-08-03 |
US20180358562A1 (en) | 2018-12-13 |
JPWO2017103732A1 (ja) | 2018-11-08 |
WO2017103732A1 (ja) | 2017-06-22 |
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