JP2015118977A - 受光層形成方法及び有機光電変換素子の製造方法、成膜用有機材料及びそれを用いて得られた有機光電変換素子、光センサ。 - Google Patents
受光層形成方法及び有機光電変換素子の製造方法、成膜用有機材料及びそれを用いて得られた有機光電変換素子、光センサ。 Download PDFInfo
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- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound 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
- UNJZLNFHHINVOB-UHFFFAOYSA-N n-naphthalen-1-ylnaphthalen-2-amine Chemical compound C1=CC=C2C(NC=3C=C4C=CC=CC4=CC=3)=CC=CC2=C1 UNJZLNFHHINVOB-UHFFFAOYSA-N 0.000 description 1
- SBMXAWJSNIAHFR-UHFFFAOYSA-N n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(NC=3C=C4C=CC=CC4=CC=3)=CC=C21 SBMXAWJSNIAHFR-UHFFFAOYSA-N 0.000 description 1
- 239000002071 nanotube Substances 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000004095 oxindolyl group Chemical class N1(C(CC2=CC=CC=C12)=O)* 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000035515 penetration Effects 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
- 239000012466 permeate Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical group C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical group N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 238000004549 pulsed laser deposition Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical group C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000005477 sputtering target 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
- 238000003860 storage Methods 0.000 description 1
- 230000007847 structural defect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- VELSFHQDWXAPNK-UHFFFAOYSA-N tetracontacyclo[25.6.5.516,28.44,32.35,11.321,34.28,10.212,15.222,35.229,31.113,20.124,38.02,6.014,19.017,25.018,23.030,37.033,36.547,54.446,53.448,58.126,51.150,52.03,45.07,42.09,61.039,40.041,43.044,63.049,76.055,78.056,62.057,68.059,64.060,67.065,69.066,71.070,73.072,75.074,77]octaheptaconta-1,3(45),4(48),5(61),6,8,10,12,14,16,18,20,22,24(39),25,27(38),28,30,32,34(42),35(40),36,41(43),44(63),46,49(76),50(77),51,53,55(78),56(62),57,59,64,66,68,70(73),71,74-nonatriacontaene Chemical compound c12c3c4c5c6c1c1c7c8c2c2c3c3c9c4c4c5c5c%10c%11c%12c%13c%14c%15c%12c%12c%16c%17c%18c%19c%20c%21c%17c%17c%22c%21c%21c%23c%20c%20c%19c%19c%24c%18c%16c%15c%15c%24c%16c(c7c%15c%14c1c6c5%13)c8c1c2c2c3c3c(c%21c5c%22c(c%11c%12%17)c%10c4c5c93)c%23c2c%20c1c%19%16 VELSFHQDWXAPNK-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
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- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
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- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
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Abstract
Description
光センサに用いられる有機光電変換素子の受光層を乾式成膜にて成膜する受光層形成方法において、
受光層の構成有機物からなる蛍光量子収率が0.2以上の粉粒体からなる成膜用有機材料を少なくとも1種用意し、
この成膜用有機材料からなる気化源を用いて乾式成膜を実施するものである。
受光層の構成有機物からなる蛍光量子収率が0.2以上の粉粒体からなるものである。
また、本明細書において、「構成有機物」とは、成膜用有機材料中に含まれる有機物のうち、不可避不純物及び成膜用有機材料中に意図せずに含まれた物質を除く全ての有機物を意味する。
図面を参照して、本発明にかかる一実施形態の光電変換素子について説明する。図1は、本実施形態の光電変換素子の構成を示す概略断面図である。本明細書の図面において、視認しやすくするため、各部の縮尺は適宜変更して示してある。
受光層30は、光電変換層32を少なくとも含む層であればよいが、本実施形態では、下部電極20と光電変換層32との間に電子ブロッキング層31を備えている。受光層30は、光電変換層32、電子ブロッキング層31以外の層(例えば正孔ブロッキング層)を含む層であってもよい。
基板10としては特に制限なく、シリコン基板、ガラス基板等を用いることができる。
受光層30は、少なくとも光電変換層32を含む有機層であり、成膜用有機材料60を用いて、乾式成膜法により成膜された有機層を含む。本実施形態では、受光層30は、電子ブロッキング層31と光電変換層32とにより構成されており、これらのいずれか又は両方が成膜用有機材料60を用いて乾式成膜法により成膜されている。より画素欠陥の混入及びそのばらつきを抑制するためには、受光層30に含まれる有機層ができるだけ多くの層が成膜用有機材料60を用いて成膜されることが好ましい。
光電変換層32は、光を受光し、その光量に応じた電荷を発生するものであり、有機の光電変換材料を含んで構成されている。
Z4は少なくとも2つの炭素原子を含む環であって、5員環、6員環、又は、5員環及び6員環の少なくともいずれかを含む縮合環を表す。5員環、6員環、又は、5員環及び6員環の少なくともいずれかを含む縮合環としては、通常メロシアニン色素で酸性核として用いられるものが好ましく、その具体例としては例えば以下のものが挙げられる。
(a)1,3−ジカルボニル核:例えば1,3−インダンジオン核、1,3−シクロヘキサンジオン、5,5−ジメチル−1,3−シクロヘキサンジオン、1,3−ジオキサン−4,6−ジオン等。
(b)ピラゾリノン核:例えば1−フェニル−2−ピラゾリン−5−オン、3−メチル−1−フェニル−2−ピラゾリン−5−オン、1−(2−ベンゾチアゾイル)−3−メチル−2−ピラゾリン−5−オン等。
(c)イソオキサゾリノン核:例えば3−フェニル−2−イソオキサゾリン−5−オン、3−メチル−2−イソオキサゾリン−5−オン等。
(d)オキシインドール核:例えば1−アルキル−2,3−ジヒドロ−2−オキシインドール等。
(e)2,4,6−トリケトヘキサヒドロピリミジン核:例えばバルビツル酸又は2−チオバルビツル酸及びその誘導体等。誘導体としては例えば1−メチル、1−エチル等の1−アルキル体、1,3−ジメチル、1,3−ジエチル、1,3−ジブチル等の1,3−ジアルキル体、1,3−ジフェニル、1,3−ジ(p−クロロフェニル)、1,3−ジ(p−エトキシカルボニルフェニル)等の1,3−ジアリール体、1−エチル−3−フェニル等の1−アルキル−1−アリール体、1,3−ジ(2―ピリジル)等の1,3位ジヘテロ環置換体等が挙げられる。
(f)2−チオ−2,4−チアゾリジンジオン核:例えばローダニン及びその誘導体等。誘導体としては例えば3−メチルローダニン、3−エチルローダニン、3−アリルローダニン等の3−アルキルローダニン、3−フェニルローダニン等の3−アリールローダニン、3−(2−ピリジル)ローダニン等の3位ヘテロ環置換ローダニン等が挙げられる。
(g)2−チオ−2,4−オキサゾリジンジオン(2−チオ−2,4−(3H,5H)−オキサゾールジオン核:例えば3−エチル−2−チオ−2,4−オキサゾリジンジオン等。
(h)チアナフテノン核:例えば3(2H)−チアナフテノン−1,1−ジオキサイド等。
(i)2−チオ−2,5−チアゾリジンジオン核:例えば3−エチル−2−チオ−2,5−チアゾリジンジオン等。
(j)2,4−チアゾリジンジオン核:例えば2,4−チアゾリジンジオン、3−エチル−2,4−チアゾリジンジオン、3−フェニル−2,4−チアゾリジンジオン等。
(k)チアゾリン−4−オン核:例えば4−チアゾリノン、2−エチル−4−チアゾリノン等。
(l)2,4−イミダゾリジンジオン(ヒダントイン)核:例えば2,4−イミダゾリジンジオン、3−エチル−2,4−イミダゾリジンジオン等。
(m)2−チオ−2,4−イミダゾリジンジオン(2−チオヒダントイン)核:例えば2−チオ−2,4−イミダゾリジンジオン、3−エチル−2−チオ−2,4−イミダゾリジンジオン等。
(n)2−イミダゾリン−5−オン核:例えば2−プロピルメルカプト−2−イミダゾリン−5−オン等。
(o)3,5−ピラゾリジンジオン核:例えば1,2−ジフェニル−3,5−ピラゾリジンジオン、1,2−ジメチル−3,5−ピラゾリジンジオン等。
(p)ベンゾチオフェン−3−オン核:例えばベンゾチオフェン−3−オン、オキソベンゾチオフェンー3−オン、ジオキソベンゾチオフェンー3−オン等。
(q)インダノン核:例えば1−インダノン、3−フェニル−1−インダノン、3−メチル−1−インダノン、3,3−ジフェニル−1−インダノン、3,3−ジメチル−1−インダノン等。
(r)ベンゾフラン−3−(2H)-オン核:例えば、ベンゾフラン−3−(2H)−オン等。
(s)2,2−ジヒドロフェナレン−1,3−ジオン核等。
これらはさらに置換基Wを有していてもよく、さらに他の環が縮環していてもよい。
L1、L2、及びL3はそれぞれ独立に、無置換メチン基、又は置換メチン基を表す。置換メチン基同士が結合して環(例、6員環例えばベンゼン環)を形成してもよい。置換メチン基の置換基は置換基Wが挙げられる。
置換基Wは後述する。
nは0以上の整数を表し、好ましくは0〜3の整数を表し、より好ましくは0〜2である。
D1は原子群を表す。例えば、トリアリールアミン化合物、ベンジジン化合物、ピラゾリン化合物、スチリルアミン化合物、ヒドラゾン化合物、トリフェニルメタン化合物、カルバゾール化合物等を用いることが好ましい。
R1としてはアルキル基、アリール基がより好ましい。R6及びR7としては、シアノ基がより好ましい。
受光層30に含まれる電子ブロッキング層31は、下部電極20から光電変換層32に電子が注入されるのを抑制し、光電変換層32で発生した電子が電極2側に流れるのを阻害するための層である。電子ブロッキング層31は、有機材料又は無機材料、あるいはその両方を含んで構成されている。
すが、本発明はこれらに限定されるものではない。なお、下記のEaはその材料の電子親
和力、Ipはその材料のイオン化ポテンシャルを示す。EB―1,2,…の「EB」は
「電子ブロッキング」の略である。
としては、1,3−ビス(4−tert−ブチルフェニル−1,3,4−オキサジアゾリ
ル)フェニレン(OXD−7)等のオキサジアゾール誘導体、アントラキノジメタン誘導
体、ジフェニルキノン誘導体、バソクプロイン、バソフェナントロリン、及びこれらの誘
導体、トリアゾール化合物、トリス(8−ヒドロキシキノリナート)アルミニウム錯体、
ビス(4−メチル−8−キノリナート)アルミニウム錯体、ジスチリルアリーレン誘導
体、シロール化合物などを用いることができる。また、電子受容性有機材料でなくとも、
十分な電子輸送性を有する材料ならば使用することは可能である。ポルフィリン系化合物
や、DCM(4−ジシアノメチレン−2−メチル−6−(4−(ジメチルアミノスチリ
ル))−4Hピラン)等のスチリル系化合物、4Hピラン系化合物を用いることができ
る。
封止層50は、水、酸素等の有機材料を劣化させる因子が有機材料を含む受光層に侵入するのを防ぐための層である。封止層50は、下部電極20、電子ブロッキング層31、光電変換層32、及び上部電極40を覆って形成されている。
以上のように、光電変換素子1は構成されている。
次に、光電変換素子1を備えた撮像素子(光センサ)100の構成について、図3を参照して説明する。図3は、本発明の一実施形態を説明するための撮像素子の概略構成を示す断面模式図である。この撮像素子は、デジタルカメラ、デジタルビデオカメラ等の撮像装置、電子内視鏡、携帯電話機等の撮像モジュール等に搭載して用いられる。
(化合物1)
まず、化合物1の成膜用有機材料を調製した。
化合物1の合成は、下記反応式に示される工程に準じて実施した。
脱水キシレンにN−フェニル−2−ナフチルアミン(東京化成社製)、6―ブロモ―2−ナフトエ酸メチル(和光純薬社製)、酢酸パラジウム、トリフェニルホスフィン、炭酸セシウムを加え、3時間還流した。反応混合物を吸引ろ過し、溶媒をエバポレーターで留去した後、シリカゲルカラムによって精製した(展開溶媒:トルエン)。溶媒を留去することにより、化合物(1a)を得た。
脱水トルエンにSMEAH(水素化ビス(2−メトキシエトキシ)アルミニウムナトリウム・トルエン溶液(約70%)(和光純薬社製))を加え、内温を氷浴で0℃にした後、1−メチルピペラジンを脱水トルエンに溶かした溶液を滴下した。脱水トルエンに化合物(1a)を溶かし、内温をドライアイス浴で−40℃にした後、これに、上記で調整したSMEAHトルエン溶液を滴下した。4.5時間攪拌した後、濃塩酸をpHが1になるまで加えた。これに水、酢酸エチルを加え油層を炭酸水素ナトリウム水溶液で洗浄した。油層を硫酸マグネシウムで乾燥させた後、ろ過し、エバポレーターによって溶媒を留去した。反応混合物をシリカゲルカラムによって精製し、溶媒を留去することにより、化合物(1b)を得た。
化合物(1b)とベンゾインダンジオンをトルエンとエタノールの混合溶媒に加え、2時間還流した。放冷後、吸引ろ過を行うことで、化合物(1)を得た。
次に、得られた化合物1(粗体)を精製する。この精製工程において、精製を繰り返す、または精製方法を複数組み合わせて実施し、蛍光量子収率値の異なる化合物1が得られた。[精製方法例:得られた化合物を溶媒中(少量のクロロホルム)に分散させ、洗浄した。または溶媒(少量のクロロホルム)に溶解させ、エタノールで再結晶させた。または昇華精製を実施した。
精製工程については化合物1と同様にして、化合物2〜11からなる成膜用有機材料の調製を行った。
化合物2の合成は、下記反応式に示される工程に準じて実施した。
化合物1において、N−フェニル−2−ナフチルアミンを1,2’−ジナフチルアミン(東京化成社製)に変更すること以外は同様にして合成した。
化合物1において、N−フェニル−2−ナフチルアミンを2,2’−ジナフチルアミン(東京化成社製)に変更すること以外は同様にして合成した。
化合物1において、1bを4−(N、N’−ジフェニルアミノ)ベンズアルデヒドを(東京化成社製)に変更すること以外は同様にして合成した。
Chem. Matter. 2001年, 13巻, 456-458貢おけるDCTPであり、該論文を参考にして合成した。
化合物1において、N−フェニル−2−ナフチルアミンをN−(2,4,6−トリメチルフェニル)−4−ビフェニルアミンに変更すること以外は同様にして合成した。
実施例1〜3,比較例1〜2の各例で用いた化合物1について、蛍光量子収率の値と共に表1に示す。各例の蛍光量子収率は、各例の粉粒体10mgを用い、浜松ホトニクス社製;絶対蛍光量子収率測定装置(型番:C9920-02)にて測定した。
同様に実施例4〜13,比較例3〜16の各例で用いた化合物2〜11について、蛍光量子収率の値と共に表1に示す。
ガラス基板を用意し、基板上に、アモルファス性ITO下部電極(30nm厚)をスパッタ法により成膜し、次いで、電子ブロッキング層として上記EB−3を抵抗加熱蒸着法により成膜した(100nm厚)。
次いで、各例において、化合物1(表1に蛍光量子収率を記載)とフラーレン(C60)を光電変換層用成膜用有機材料としてそれぞれ用意し、電子ブロッキング層上に抵抗加熱蒸着法により膜厚500nmとなるように共蒸着して成膜した。
得られた各光電変換素子に中心波長525nmのLED光を上部電極(透明導電性膜)側から入射した。光電変換素子に、2×105V/cmの電場で印加し、入射したLED光をオフにした時間から0.1秒後における残像電流値を評価した。評価結果を下記表1に示す。
同様に、化合物2〜11で蛍光量子収率の異なる化合物を用いて光電変換素子を作製し、実施例4〜13,比較例3〜16の残像電流値を得た。精製に使用した溶媒はクロロホルム、トルエン、塩化メチレンから適時選択した。使用した各材料のおよび電子ブロッキング層EB-3のHPLC純度は各99.5%以上である。
表1において、残像電流値は、実施例6の値を基準値10とし、相対値で示した。
10,101,210 基板
20 下部電極
30 受光層
31 電子ブロッキング層
32 光電変換層
40 上部電極
50 封止層
60 蒸着材料(成膜用有機材料)
71 蒸着セル
100 撮像素子,光センサ
106 信号読み出し回路
200 有機電界発光素子
221 陽極
222 陰極
234 発光層
Claims (18)
- 光センサに用いられる有機光電変換素子の受光層を乾式成膜にて成膜する受光層形成方法において、
前記受光層の構成有機物からなる、蛍光量子収率が0.2以上の粉粒体からなる成膜用有機材料を少なくとも1種用意し、
該成膜用有機材料を含む気化源を用いて前記乾式成膜を実施する受光層形成方法。 - 前記粉粒体の蛍光量子収率は、0.2以上0.4以下である請求項1記載の受光層形成方法。
- 前記構成有機物がp型有機半導体材料である請求項1又は2いずれか1項に記載の受光層形成方法。
- 前記構成有機物が、下記式(A)アミン部位、または、下記式(B)カルボニル基部位を1つ以上有する請求項1〜3いずれか1項記載の受光層形成方法。
式(B)式中、Y1は、2つ以上の炭素原子を含む環であって、5員環、6員環、又は、5員環及び6員環の少なくともいずれかを含む縮合環を表し、これは置換基を有してもよい。) - 前記構成有機物が、下記式(C)である請求項1〜4いずれか1項記載の受光層形成方法。
- 前記乾式成膜法が抵抗加熱蒸着法である請求項1〜5いずれか1項記載の受光層形成方法。
- 前記受光層が光電変換層である請求項1〜6いずれか1項記載の受光層形成方法。
- 一対の電極と、前記一対の電極に挟持された少なくとも光電変換層を含む受光層を有する有機光電変換素子の製造方法であって、
前記受光層を請求項1〜7いずれか1項記載の受光層形成方法により成膜する有機光電変換素子の製造方法。 - 有機光電変換素子の受光層の乾式成膜に用いられ、
前記受光層の構成有機物からなる蛍光量子収率が0.2以上の粉粒体からなる成膜用有機材料。 - 前記蛍光量子収率が0.2以上0.4以下である請求項9記載の成膜用有機材料。
- 前記構成有機物がp型有機半導体材料である請求項9又は10いずれか1項に記載の成膜用有機材料。
- 前記粉粒体の平均粒径が50μm以上800μm以下で請求項11に記載の成膜用有機材料。
- 前記構成有機物が、下記式(A)アミン部位、または、下記式(B)カルボニル基部位を1つ以上有する請求項9〜12いずれか1項記載の成膜用有機材料。
式(B)式中、Y1は、2つ以上の炭素原子を含む環であって、5員環、6員環、又は、5員環及び6員環の少なくともいずれかを含む縮合環を表し、これは置換基を有してもよい。) - 前記構成有機物が、下記式(C)である請求項9〜13いずれか1項記載の成膜用有機材料。
- 前記乾式成膜法が抵抗加熱蒸着法である請求項9〜14いずれか1項記載の成膜用有機材料。
- 一対の電極と、該一対の電極に挟持された少なくとも光電変換層を含む受光層を有する有機光電変換素子であって、
前記光電変換層が請求項9〜請求項15のいずれか1項記載の成膜用有機材料を用いて乾式成膜されてなる有機光電変換素子。 - 複数の、請求項16に記載の有機光電変換素子と、
該光電変換素子の前記光電変換層で発生した電荷に応じた信号を読み出す信号読出し回路が形成された回路基板とを備える光センサ。 - 撮像素子である請求項17に記載の光センサ。
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JP2013023752A (ja) * | 2011-07-25 | 2013-02-04 | Fujifilm Corp | 光電変換素子用蒸着材料及び光電変換素子、センサ、撮像素子 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2019176754A1 (ja) * | 2018-03-12 | 2019-09-19 | 富士フイルム株式会社 | 光電変換素子、撮像素子、光センサ、化合物 |
JPWO2019176754A1 (ja) * | 2018-03-12 | 2021-02-18 | 富士フイルム株式会社 | 光電変換素子、撮像素子、光センサ、化合物 |
JPWO2020202978A1 (ja) * | 2019-03-29 | 2020-10-08 | ||
WO2020202978A1 (ja) * | 2019-03-29 | 2020-10-08 | 富士フイルム株式会社 | 光電変換素子、撮像素子、光センサ、撮像素子用光電変換素子用材料、光センサ用光電変換素子用材料 |
WO2020261933A1 (ja) * | 2019-06-28 | 2020-12-30 | 富士フイルム株式会社 | 光電変換素子、撮像素子、光センサ、光電変換素子用材料 |
WO2021141078A1 (ja) | 2020-01-10 | 2021-07-15 | 富士フイルム株式会社 | 光電変換素子、撮像素子、光センサ |
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KR101869620B1 (ko) | 2018-07-23 |
TW201529875A (zh) | 2015-08-01 |
JP6145883B2 (ja) | 2017-06-14 |
KR20160071465A (ko) | 2016-06-21 |
WO2015093049A1 (ja) | 2015-06-25 |
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