JP4618414B2 - 有機材料および有機電界発光素子 - Google Patents
有機材料および有機電界発光素子 Download PDFInfo
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- JP4618414B2 JP4618414B2 JP2004280868A JP2004280868A JP4618414B2 JP 4618414 B2 JP4618414 B2 JP 4618414B2 JP 2004280868 A JP2004280868 A JP 2004280868A JP 2004280868 A JP2004280868 A JP 2004280868A JP 4618414 B2 JP4618414 B2 JP 4618414B2
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- 125000001424 substituent group Chemical group 0.000 claims description 33
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- 125000003118 aryl group Chemical group 0.000 claims description 23
- 238000005401 electroluminescence Methods 0.000 claims description 17
- 238000006471 dimerization reaction Methods 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
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- 230000000447 dimerizing effect Effects 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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- 150000002367 halogens Chemical class 0.000 claims description 4
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Description
上述した一般式(1)、一般式(2)および一般式(3)で示される本発明の有機材料は、有機電界発光素子の有機層に用いられる芳香族アミン系のビフルオランテン化合物である。ビフルオランテン化合物は、各々のフルオランテンの結合位置において複数の異性体が存在するが、本発明の有機材料はその構造異性体を全て包含する。すなわち、本発明の有機材料は、ビフルオランテンの分子対称性を鑑みた、以下の15通りの組み合わせの置換様式の異性体を全て含む。
b)2、2’−ビフルオランテン;一般式(1)のA4部位とA5部位での結合
c)3、3’−ビフルオランテン;一般式(1)のA14部位とA15部位での結合
d)7、7’−ビフルオランテン;一般式(1)のA2部位とA7部位での結合
e)8、8’−ビフルオランテン;一般式(1)のA1部位とA8部位での結合
f)1、2’−ビフルオランテン;一般式(1)のA3部位とA5部位での結合
g)1、3’−ビフルオランテン;一般式(1)のA3部位とA13部位での結合
h)1、7’−ビフルオランテン;一般式(1)のA3部位とA7部位での結合
i)1、8’−ビフルオランテン;一般式(1)のA3部位とA8部位での結合
j)2、3’−ビフルオランテン;一般式(1)のA4部位とA13部位での結合
k)2、7’−ビフルオランテン;一般式(1)のA4部位とA7部位での結合
l)2、8’−ビフルオランテン;一般式(1)のA4部位とA8部位での結合
m)3、7’−ビフルオランテン;一般式(1)のA15部位とA7部位での結合
n)3、8’−ビフルオランテン;一般式(1)のA15部位とA8部位での結合
o)7、8’−ビフルオランテン;一般式(1)のA2部位とA8部位での結合
a)ハロゲン化されたフルオランテンを、マグネシウムを用いたグリニヤー反応によってカップリングさせる合成方法。
b)ハロゲン化されたフルオランテンを、銅触媒存在下でウルマン反応によってカップリングさせる方法。
c)ボロン酸、もしくはボロン酸エステル化されたフルオランテンとハロゲン化されたフルオランテンとを、パラジウムに代表される遷移金属触媒によってカップリングさせる(いわゆる鈴木カップリング反応)によって合成させる方法。
a)有機材料を合成した後、速やかに冷所に静置させる。その保管温度は−100℃から100℃の範囲が好ましく、より好ましくは−50℃から50℃の温度範囲で保管させる。
b)有機材料を合成した後、速やかに遮光性を有する容器に保管する。
c)有機材料を合成した後、合成した有機材料を窒素、二酸化炭素、アルゴンなどの不活性ガス雰囲気下で保管する。
次に、上述した有機材料を用いた有機電界発光素子(有機EL素子)の構成を、図2に基づいて詳細に説明する。
表1の構造式(1)で示した8−N,N−ジフェニルアミノ−3,3’―ビフルオランテンを次の手順で合成した。
表1の構造式(5)で示した8,8’−ビス(N,N−ジフェニルアミノ)−3,3’-ビフルオランテンを次の手順で合成した。
表1の構造式(28)で示した3,3’―ビス(N−2−ナフチルーN−フェニルアミノ)−8,8’―ビフルオランテンを次の手順で合成した。
合成例1によって得られた8−N,N−ジフェニルアミノ−3,3’―ビフルオランテン[表1の構造式(1)]を用い、以下のように有機電界発光素子(図2参照)を作製した。
実施例1記載の発光層14cの有機材料として、上記表7に記載した各構造式の化合物をした使用したほかは、実施例1と全く同様に有機電界発光素子を作製し、同様の評価を行った。尚、表7には、評価結果も合わせて示した。
実施例1記載の正孔輸送層14bの有機材料として、下記構造式(34)に示す3−N,N−ジフェニルアミノフルオランテン(特開平10−125467号公報参照)を使用した他は、実施例1と全く同様に有機電界発光素子を作製し同じく評価を行った。その結果を合わせて上記表7に示した。
実施例1記載の発光層14cとして、下記構造式(35)に示される9,10−ジ(2−ナフチル)アントラセン(ADN)を蒸着し、膜厚50nmの膜を形成した。その際、ADNには合成例1で製造された8−N,N−ジフェニルアミノ−3,3’―ビフルオランテン[表1の構造式(1)]を相対膜厚比(すなわち体積比)8体積%でドーピングして発光層14cとした。
実施例4記載におけるADNに対する8−N,N−ジフェニルアミノ−3,3’―ビフルオランテン[表1の構造式(1)]のドーピング濃度を、上記表8記載の濃度に変更した以外は、実施例4と同様な素子構成として評価を行った。その結果を合わせて上記表8に示した。
Claims (9)
- 下記一般式(1)で示されるフルオランテンを二量化したビフルオランテン構造を有し、前記一般式(1)で示される分子内に下記一般式(2)または一般式(3)で示される置換基を少なくとも一つ含有する有機電界発光素子用の有機材料。
- 請求項1記載の有機材料において、
前記一般式(1)におけるA1〜A4およびA15〜A20のうちの少なくとも1つと、A5〜A14のうちの少なくとも1つは、前記一般式(2)または一般式(3)の置換基を示す、有機材料。 - 請求項1記載の有機材料において、
前記一般式(1)におけるA1、A2、A19、およびA20のうちの1つと、A7〜A10のうちの1つは、前記一般式(2)または一般式(3)の置換基を示す、有機材料。 - 陽極と陰極との間に有機層を狭持してなる有機電界発光素子において、
前記有機層が、下記一般式(1)で示されるフルオランテンを二量化したビフルオランテン構造を有し、前記一般式(1)で示される分子内に下記一般式(2)または一般式(3)で示される置換基を少なくとも一つ含有する有機材料を用いて構成されている有機電界発光素子。
- 請求項4記載の有機電界発光素子において、
前記一般式(1)におけるA1〜A4およびA15〜A20のうちの少なくとも1つと、A5〜A14のうちの少なくとも1つは、前記一般式(2)または一般式(3)の置換基を示す、有機電界発光素子。 - 請求項4記載の有機電界発光素子において、
前記一般式(1)におけるA1、A2、A19、およびA20のうちの1つと、A7〜A10のうちの1つは、前記一般式(2)または一般式(3)の置換基を示す、有機電界発光素子。 - 請求項4記載の有機電界発光素子において、
前記有機層が、二量化に用いられないA 1 〜A 20 のうちの少なくとも1ヶ所に前記一般式(2)で示される置換基を有する前記一般式(1)で示しされる有機材料を用いて構成された正孔輸送層を備えている、有機電界発光素子。 - 請求項4記載の有機電界発光素子において、
前記有機層が、二量化に用いられないA 1 〜A 20 のうちの少なくとも1ヶ所に前記一般式(2)で示される置換基を有する前記一般式(1)で示しされる有機材料を用いて構成された発光層を備えている、有機電界発光素子。 - 請求項8記載の有機電界発光素子において、
前記発光層に、二量化に用いられないA 1 〜A 20 のうちの少なくとも1ヶ所に前記一般式(2)で示される置換基を有する前記一般式(1)で示しされる有機材料が30体積%以下の割合で含まれている、有機電界発光素子。
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