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JP2003109758A5
JP2003109758A5 JP2001296657A JP2001296657A JP2003109758A5 JP 2003109758 A5 JP2003109758 A5 JP 2003109758A5 JP 2001296657 A JP2001296657 A JP 2001296657A JP 2001296657 A JP2001296657 A JP 2001296657A JP 2003109758 A5 JP2003109758 A5 JP 2003109758A5
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【特許請求の範囲】
【請求項１】 下記一般式（１）で表され、Ｎ−Ｍ−Ｙ−Ｚの２面角（即ち２つの環のねじれ角）が９度以上９０度未満である金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。
【化１】

Figure 2003109758
［式中、Ｎは窒素原子、Ｃは炭素原子を表し、Ｘは炭素原子、窒素原子または酸素原子を表し、Ｍは炭素原子または窒素原子を表し、Ｙは炭素原子または窒素原子を表し、Ｚは炭素原子または窒素原子を表し、ＡはＸ−Ｍ−Ｎと共に５〜６員の複素環を形成するのに必要な原子群を表し、ＢはＣ−Ｙ−Ｚと共に５〜６員の炭化水素環または複素環を形成するのに必要な原子群を表す。また、２つの環はそれぞれ独立に置換基を有していても良く、隣接する置換基同士でさらに縮合環を形成してもよい。Ｍｅはイリジウム、プラチナまたはオスミウムを表す。ｎは１、２、３又は４を表し、ｍは、Ｍｅがイリジウムの時３−ｎを、プラチナの時４−ｎ又は２−ｎを、オスミウムの時２−ｎを表す。Ｗ1は酸素原子、窒素原子または硫黄原子を表し、Ｗ2は酸素原子、窒素原子または硫黄原子を表し、Ｌ1は窒素原子または炭素原子を表し、Ｌ2は窒素原子または酸素原子を表し、ｌは１または２を表す。なお、Ｗ1とＬ1、Ｌ1とＬ2、Ｌ2とＬ2（ｌが２の時）、Ｌ2とＷ2の結合は単結合でも二重結合でもよい。］
【請求項２】 下記一般式（３）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。
【化Ａ】
Figure 2003109758
［式中、Ｎは窒素原子、Ｃは炭素原子を表し、Ｘは炭素原子、窒素原子又は酸素原子を表し、Ｍは炭素原子または窒素原子を表し、Ｙは炭素原子または窒素原子を表し、Ｚは炭素原子または窒素原子を表し、Ｔは炭素原子または窒素原子を表し、ＡはＸ−Ｍ−Ｎと共に５〜６員の複素環を形成するのに必要な原子群を表し、Ｂ 2 はＣ−Ｙ−Ｚ−Ｔと共に５〜６員の炭化水素環または複素環を形成するのに必要な原子群を表し、Ｂ 3 はＺ−Ｔと共に５〜６員の炭化水素環または複素環を形成するのに必要な原子群を表す。Ｍｅはイリジウム、プラチナまたはオスミウムを表す。ｎは１、２、３又は４を表し、ｍは、Ｍｅがイリジウムの時３−ｎを、プラチナの時４−ｎ又は２−ｎを、オスミウムの時２−ｎを表す。Ｗ 1 は酸素原子、窒素原子または硫黄原子を表し、Ｗ 2 は酸素原子、窒素原子または硫黄原子を表し、Ｌ 1 は窒素原子または炭素原子を表し、Ｌ 2 は窒素原子または酸素原子を表し、ｌは１または２を表す。なお、Ｗ 1 とＬ 1 、Ｌ 1 とＬ 2 、Ｌ 2 とＬ 2 （ｌが２の時）、Ｌ 2 とＷ 2 の結合は単結合でも二重結合でもよい。］
【請求項３】 下記一般式（４）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。
【化Ｂ】
Figure 2003109758
［式中、Ｎは窒素原子、Ｃは炭素原子を表し、Ｘは炭素原子、窒素原子、酸素原子または硫黄原子を表し、Ｍは炭素原子または窒素原子を表し、Ｙは炭素原子または窒素原子を表し、Ｚは炭素原子または窒素原子を表し、ＡはＸ−Ｍ−Ｎと共に５〜６員の芳香族複素環を形成するのに必要な原子群を表し、ＢはＣ−Ｙ−Ｚと共に５〜６員の芳香族炭化水素環または芳香族複素環を形成するのに必要な原子群を表す。ただし、Ｘ−Ｍ−ＮとＡで形成される芳香族複素環およびＣ−Ｙ−ＺとＢで形成される芳香族炭化水素環または芳香族複素環は少なくとも１つの置換基で置換されており、かつ、該置換基のσｐ値の総和は０．１５以上２以下である。ＥＷＧ１およびＥＷＧ２はそれぞれ独立にハメットに置換基定数σｐ値が０以上の電子吸引性基を表し、σｐ値の総和は０．１５以上２以下である。Ｓ１は０〜３の整数を表し、Ｓ２は０〜３の整数を表す。ただしＳ１とＳ２の和は１以上５以下である。Ｍｅはイリジウム、プラチナまたはオスミウムを表す。ｎは１、２、３又は４を表し、ｍは、Ｍｅがイリジウムの時３−ｎを、プラチナの時４−ｎ又は２−ｎを、オスミウムの時２−ｎを表す。Ｗ 1 は酸素原子、窒素原子または硫黄原子を表し、Ｗ 2 は酸素原子、窒素原子または硫黄原子を表し、Ｌ 1 は窒素原子または炭素原子を表し、Ｌ 2 は窒素原子または酸素原子を表し、ｌは１または２を表す。なお、Ｗ 1 とＬ 1 、Ｌ 1 とＬ 2 、Ｌ 2 とＬ 2 （ｌが２の時）、Ｌ 2 とＷ 2 の結合は単結合でも二重結合でもよい。］
【請求項４】 前記一般式（４）において、Ｎ−Ｍ−Ｙ−Ｚの２面角（即ち２つの環のねじれ角）が９度以上９０度未満であることを特徴とする請求項３に記載の有機エレクトロルミネッセンス素子。
【請求項５】 下記一般式（５）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。
【化Ｃ】
Figure 2003109758
［式中、Ｎは窒素原子、Ｘは炭素原子、窒素原子、酸素原子または硫黄原子を表し、Ｍは炭素原子または窒素原子を表し、ＡはＸ−Ｍ−Ｎと共に５〜６員の芳香族複素環を形成するのに必要な原子群を表し、Ｒ 61 は立体パラメータＥｓ値が−０．６以下の置換基を表し、Ｒ 62 、Ｒ 63 及びＲ 64 は水素原子または置換基を表す。また、Ｘ−Ｍ−ＮとＡとで形成される芳香族複素環は置換基を有していても良く、隣接する置換基同士で縮合環を形成してもよい。Ｍｅはイリジウム、プラチナまたはオスミウムを表す。ｎは１、２、３又は４を表し、ｍは、Ｍｅがイリジウムの時３−ｎを、プラチナの時４−ｎ又は２−ｎを、オスミウムの時２−ｎを表す。Ｗ 1 は酸素原子、窒素原子または硫黄原子を表し、Ｗ 2 は酸素原子、窒素原子または硫黄原子を表し、Ｌ 1 は窒素原子または炭素原子を表し、Ｌ 2 は窒素原子または酸素原子を表し、ｌは１または２を表す。なお、Ｗ 1 とＬ 1 、Ｌ 1 とＬ 2 、Ｌ 2 とＬ 2 （ｌが２の時）、Ｌ 2 とＷ 2 の結合は単結合でも二重結合でもよい。］
【請求項６】 下記一般式（６）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。
【化Ｄ】
Figure 2003109758
［式中、Ｒ 71 、Ｒ 75 は水素原子または置換基を表し、Ｒ 71 とＲ 75 の少なくとも一方は置換基を表す。またＲ 71 とＲ 75 の立体パラメータＥｓ値の総和は−０．６以下である。Ｒ 72 、Ｒ 73 、Ｒ 74 、Ｒ 76 、Ｒ 77 及びＲ 78 は水素原子または置換基を表す。また、隣接する置換基同士は互いに結合して縮合環を形成してもよい。Ｍｅはイリジウム、プラチナまたはオスミウムを表す。ｎは１、２、３又は４を表し、ｍは、Ｍｅがイリジウムの時３−ｎを、プラチナの時４−ｎ又は２−ｎを、オスミウムの時２−ｎを表す。Ｗ 1 は酸素原子、窒素原子または硫黄原子を表し、Ｗ 2 は酸素原子、窒素原子または硫黄原子を表し、Ｌ 1 は窒素原子または炭素原子を表し、Ｌ 2 は窒素原子または酸素原子を表し、ｌは１または２を表す。なお、Ｗ 1 とＬ 1 、Ｌ 1 とＬ 2 、Ｌ 2 とＬ 2 （ｌが２の時）、Ｌ 2 とＷ 2 の結合は単結合でも二重結合でもよい。］
【請求項７】 下記一般式（７）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。
【化Ｅ】
Figure 2003109758
［式中、Ａｒは芳香族基を表し、Ｒ 81 〜Ｒ 87 は水素原子または置換基を表す。また、隣接する置換基同士は互いに結合して縮合環を形成してもよい。Ｍｅはイリジウムまたはプラチナまたはオスミウムを表す。ｎは１、２、３又は４を表し、ｍは、Ｍｅがイリジウムの時３−ｎを、プラチナの時４−ｎ又は２−ｎを、オスミウムの時２−ｎを表す。Ｗ 1 は酸素原子、窒素原子または硫黄原子を表し、Ｗ 2 は酸素原子、窒素原子または硫黄原子を表し、Ｌ 1 は窒素原子または炭素原子を表し、Ｌ 2 は窒素原子または酸素原子を表し、ｌは１または２を表す。なお、Ｗ 1 とＬ 1 、Ｌ 1 とＬ 2 、Ｌ 2 とＬ 2 （ｌが２の時）、Ｌ 2 とＷ 2 の結合は単結合でも二重結合でもよい。］
【請求項８】 下記一般式（８）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。
【化Ｆ】
Figure 2003109758
［式中、Ｎは窒素原子、Ｘは炭素原子、窒素原子、酸素原子または硫黄原子を表し、Ｍは炭素原子または窒素原子を表し、ＡはＸ−Ｍ−Ｎと共に５〜６員の芳香族複素環を形成するのに必要な原子群を表し、Ｒ 91 〜Ｒ 94 は水素原子または置換基を表す。ただし、Ｒ 91 〜Ｒ 94 のそれぞれの置換基のσｐ値の総和は０．１５以上２以下である。また、Ｘ−Ｍ−ＮとＡとで形成される芳香族複素環は置換基を有していても良く、隣接する置換基同士で縮合環を形成してもよい。Ｍｅはイリジウム、プラチナまたはオスミウムを表す。ｎは１、２、３又は４を表し、ｍは、Ｍｅがイリジウムの時３−ｎを、プラチナの時４−ｎ又は２−ｎを、オスミウムの時２−ｎを表す。Ｗ 1 は酸素原子、窒素原子または硫黄原子を表し、Ｗ 2 は酸素原子、窒素原子または硫黄原子を表し、Ｌ 1 は窒素原子または炭素原子を表し、Ｌ 2 は窒素原子または酸素原子を表し、ｌは１または２を表す。なお、Ｗ 1 とＬ 1 、Ｌ 1 とＬ 2 、Ｌ 2 とＬ 2 （ｌが２の時）、Ｌ 2 とＷ 2 の結合は単結合でも二重結合でもよい。］
【請求項９】 下記一般式（９）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。
【化Ｇ】
Figure 2003109758
［式中、Ｒ 101 〜Ｒ 106 は水素原子または置換基を表し、Ｂ 10 は２つの炭素原子と共に５〜６員の環を形成するのに必要な原子群を表す。また、隣接する置換基同士は互いに結合して縮合環を形成してもよい。Ｍｅはイリジウム、プラチナまたはオスミウムを表す。ｎは１、２、３又は４を表し、ｍは、Ｍｅがイリジウムの時３−ｎを、プラチナの時４−ｎ又は２−ｎを、オスミウムの時２−ｎを表す。Ｗ 1 は酸素原子、窒素原子または硫黄原子を表し、Ｗ 2 は酸素原子、窒素原子または硫黄原子を表し、Ｌ 1 は窒素原子または炭素原子を表し、Ｌ 2 は窒素原子または酸素原子を表し、ｌは１または２を表す。なお、Ｗ 1 とＬ 1 、Ｌ 1 とＬ 2 、Ｌ 2 とＬ 2 （ｌが２の時）、Ｌ 2 とＷ 2 の結合は単結合でも二重結合でもよい。］
【請求項１０】 前記一般式（７）のＡｒで表される芳香族基が、ハメットの置換基定数σｐ値が０．０２以上２以下の電子吸引性基で置換された芳香族炭化水素環基であることを特徴とする請求項７に記載の有機エレクトロルミネッセンス素子。
【請求項１１】 前記一般式（７）のＡｒで表される芳香族基が、ハメットの置換基定数σｐ値が０．０２以上２以下の電子吸引性基で置換された芳香族炭化水素環基であり、かつＲ 82 で表される置換基がハメットの置換規定数σｐ値が０．０２以上２以下の電子吸引性基であることを特徴とする請求項７に記載の有機エレクトロルミネッセンス素子。
【請求項１２】 前記一般式（９）のＲ 101 〜Ｒ 106 で表される置換基の少なくとも１つが、ハメットの置換規定数σｐ値が０．０２以上２以下の電子吸引性基であることを特徴とする請求項９に記載の有機エレクトロルミネッセンス素子。 [Claims]
    1. A metal complex represented by the following general formula (1) and having a dihedral angle of NMYZ (ie, twist angle of two rings) of 9 degrees or more and less than 90 degrees is used as a light emitting layer: An organic electroluminescence device containing the organic electroluminescence device.
    [Chemical 1]
Figure 2003109758
[Wherein, N represents a nitrogen atom, C represents a carbon atom, X represents a carbon atom, a nitrogen atom or an oxygen atom, M represents a carbon atom or a nitrogen atom, Y represents a carbon atom or a nitrogen atom, Z Represents a carbon atom or a nitrogen atom, A represents an atomic group necessary for forming a 5- to 6-membered heterocyclic ring with X-M-N, and B represents a 5- to 6-membered carbonization with C-Y-Z. A group of atoms necessary for forming a hydrogen ring or a heterocyclic ring is represented. The two rings may each independently have a substituent, and adjacent substituents may further form a condensed ring. Me represents iridium, platinum or osmium. n represents 1, 2, 3 or 4, and m represents 3-n when Me is iridium, 4-n or 2-n when Me is platinum, and 2-n when Me is osmium. W1Represents an oxygen atom, a nitrogen atom or a sulfur atom, and W2Represents an oxygen atom, a nitrogen atom or a sulfur atom, and L1Represents a nitrogen atom or a carbon atom, and L2Represents a nitrogen atom or an oxygen atom, and l represents 1 or 2. W1And L1, L1And L2, L2And L2(When l is 2), L2And W2The bond may be a single bond or a double bond. ]
    [Claim 2] An organic electroluminescence device comprising a light emitting layer containing a metal complex represented by the following general formula (3).
    [Chemical A]
Figure 2003109758
[Wherein, N represents a nitrogen atom, C represents a carbon atom, X represents a carbon atom, a nitrogen atom or an oxygen atom, M represents a carbon atom or a nitrogen atom, Y represents a carbon atom or a nitrogen atom, Z Represents a carbon atom or a nitrogen atom, T represents a carbon atom or a nitrogen atom, A represents an atomic group necessary for forming a 5- to 6-membered heterocyclic ring together with X-MN, and B 2 Represents an atomic group necessary for forming a 5- to 6-membered hydrocarbon ring or heterocyclic ring together with C—Y—Z—T; Three Represents an atomic group necessary for forming a 5- to 6-membered hydrocarbon ring or heterocyclic ring together with Z-T. Me represents iridium, platinum or osmium. n represents 1, 2, 3 or 4, m represents 3-n when Me is iridium, 4-n or 2-n when Me is platinum, and 2-n when Me is osmium. W 1 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and W 2 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and L 1 Represents a nitrogen atom or a carbon atom, and L 2 Represents a nitrogen atom or an oxygen atom, and l represents 1 or 2. W 1 And L 1 , L 1 And L 2 , L 2 And L 2 (When l is 2), L 2 And W 2 The bond may be a single bond or a double bond. ]
    [Claim 3] The organic electroluminescent element characterized by containing the metal complex represented by following General formula (4) in a light emitting layer.
    [Chemical B]
Figure 2003109758
[Wherein, N represents a nitrogen atom, C represents a carbon atom, X represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, M represents a carbon atom or a nitrogen atom, and Y represents a carbon atom or a nitrogen atom. Z represents a carbon atom or a nitrogen atom, A represents an atomic group necessary for forming a 5- to 6-membered aromatic heterocyclic ring with X-M-N, and B represents 5 with C-Y-Z. This represents a group of atoms necessary to form a 6-membered aromatic hydrocarbon ring or aromatic heterocycle. However, the aromatic heterocycle formed by XMN and A and the aromatic hydrocarbon ring or aromatic heterocycle formed by CYZ and B are substituted with at least one substituent. And the sum total of (sigma) p value of this substituent is 0.15 or more and 2 or less. EWG1 and EWG2 each independently represent an electron-withdrawing group having a substituent constant σp value of 0 or more in Hammett, and the sum of σp values is 0.15 or more and 2 or less. S1 represents an integer of 0 to 3, and S2 represents an integer of 0 to 3. However, the sum of S1 and S2 is 1 or more and 5 or less. Me represents iridium, platinum or osmium. n represents 1, 2, 3 or 4, m represents 3-n when Me is iridium, 4-n or 2-n when Me is platinum, and 2-n when Me is osmium. W 1 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and W 2 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and L 1 Represents a nitrogen atom or a carbon atom, and L 2 Represents a nitrogen atom or an oxygen atom, and l represents 1 or 2. W 1 And L 1 , L 1 And L 2 , L 2 And L 2 (When l is 2), L 2 And W 2 The bond may be a single bond or a double bond. ]
    [Claim 4] 4. The organic electro of claim 3, wherein in the general formula (4), a dihedral angle of NMYZ (that is, a twist angle of two rings) is 9 degrees or more and less than 90 degrees. Luminescence element.
    [Claim 5] An organic electroluminescence device comprising a light emitting layer containing a metal complex represented by the following general formula (5).
    [C]
Figure 2003109758
[Wherein, N represents a nitrogen atom, X represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, M represents a carbon atom or a nitrogen atom, and A represents a 5- to 6-membered aromatic together with X-M-N. Represents a group of atoms necessary to form a heterocycle, R 61 Represents a substituent having a steric parameter Es value of −0.6 or less, and R 62 , R 63 And R 64 Represents a hydrogen atom or a substituent. Moreover, the aromatic heterocyclic ring formed by XMN and A may have a substituent, and adjacent substituents may form a condensed ring. Me represents iridium, platinum or osmium. n represents 1, 2, 3 or 4, and m represents 3-n when Me is iridium, 4-n or 2-n when Me is platinum, and 2-n when Me is osmium. W 1 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and W 2 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and L 1 Represents a nitrogen atom or a carbon atom, and L 2 Represents a nitrogen atom or an oxygen atom, and l represents 1 or 2. W 1 And L 1 , L 1 And L 2 , L 2 And L 2 (When l is 2), L 2 And W 2 The bond may be a single bond or a double bond. ]
    [Claim 6] An organic electroluminescence device comprising a light emitting layer containing a metal complex represented by the following general formula (6).
    [Chemical D]
Figure 2003109758
[Wherein R 71 , R 75 Represents a hydrogen atom or a substituent, and R 71 And R 75 At least one of represents a substituent. Also R 71 And R 75 The sum of the three-dimensional parameter Es values is −0.6 or less. R 72 , R 73 , R 74 , R 76 , R 77 And R 78 Represents a hydrogen atom or a substituent. Further, adjacent substituents may be bonded to each other to form a condensed ring. Me represents iridium, platinum or osmium. n represents 1, 2, 3 or 4, m represents 3-n when Me is iridium, 4-n or 2-n when Me is platinum, and 2-n when Me is osmium. W 1 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and W 2 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and L 1 Represents a nitrogen atom or a carbon atom, and L 2 Represents a nitrogen atom or an oxygen atom, and l represents 1 or 2. W 1 And L 1 , L 1 And L 2 , L 2 And L 2 (When l is 2), L 2 And W 2 The bond may be a single bond or a double bond. ]
    [Claim 7] An organic electroluminescence device comprising a light emitting layer containing a metal complex represented by the following general formula (7).
    [Chemical E]
Figure 2003109758
[In the formula, Ar represents an aromatic group, R 81 ~ R 87 Represents a hydrogen atom or a substituent. Further, adjacent substituents may be bonded to each other to form a condensed ring. Me represents iridium, platinum or osmium. n represents 1, 2, 3 or 4, m represents 3-n when Me is iridium, 4-n or 2-n when Me is platinum, and 2-n when Me is osmium. W 1 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and W 2 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and L 1 Represents a nitrogen atom or a carbon atom, and L 2 Represents a nitrogen atom or an oxygen atom, and l represents 1 or 2. W 1 And L 1 , L 1 And L 2 , L 2 And L 2 (When l is 2), L 2 And W 2 The bond may be a single bond or a double bond. ]
    [Claim 8] An organic electroluminescence device comprising a light emitting layer containing a metal complex represented by the following general formula (8).
    [Chemical Formula F]
Figure 2003109758
[Wherein, N represents a nitrogen atom, X represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, M represents a carbon atom or a nitrogen atom, and A represents a 5- to 6-membered aromatic together with X-M-N. Represents a group of atoms necessary to form a heterocycle, R 91 ~ R 94 Represents a hydrogen atom or a substituent. However, R 91 ~ R 94 The sum of the σp values of the respective substituents is 0.15 or more and 2 or less. Moreover, the aromatic heterocyclic ring formed by XMN and A may have a substituent, and adjacent substituents may form a condensed ring. Me represents iridium, platinum or osmium. n represents 1, 2, 3 or 4, m represents 3-n when Me is iridium, 4-n or 2-n when Me is platinum, and 2-n when Me is osmium. W 1 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and W 2 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and L 1 Represents a nitrogen atom or a carbon atom, and L 2 Represents a nitrogen atom or an oxygen atom, and l represents 1 or 2. W 1 And L 1 , L 1 And L 2 , L 2 And L 2 (When l is 2), L 2 And W 2 The bond may be a single bond or a double bond. ]
    [Claim 9] The organic electroluminescent element characterized by containing the metal complex represented by following General formula (9) in a light emitting layer.
    [Chemical G]
Figure 2003109758
[Wherein R 101 ~ R 106 Represents a hydrogen atom or a substituent, and B Ten Represents an atomic group necessary for forming a 5- to 6-membered ring with two carbon atoms. Further, adjacent substituents may be bonded to each other to form a condensed ring. Me represents iridium, platinum or osmium. n represents 1, 2, 3 or 4, m represents 3-n when Me is iridium, 4-n or 2-n when Me is platinum, and 2-n when Me is osmium. W 1 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and W 2 Represents an oxygen atom, a nitrogen atom or a sulfur atom, and L 1 Represents a nitrogen atom or a carbon atom, and L 2 Represents a nitrogen atom or an oxygen atom, and l represents 1 or 2. W 1 And L 1 , L 1 And L 2 , L 2 And L 2 (When l is 2), L 2 And W 2 The bond may be a single bond or a double bond. ]
    [Claim 10] The aromatic group represented by Ar in the general formula (7) is an aromatic hydrocarbon ring group substituted with an electron-withdrawing group having a Hammett's substituent constant σp value of 0.02 or more and 2 or less. 8. The organic electroluminescence device according to claim 7, wherein
    11. Claims The aromatic group represented by Ar in the general formula (7) is an aromatic hydrocarbon ring group substituted with an electron-withdrawing group having a Hammett's substituent constant σp value of 0.02 or more and 2 or less, and R 82 The organic electroluminescent element according to claim 7, wherein the substituent represented by the formula is an electron-withdrawing group having a Hammett's substitution prescribed number σp value of 0.02 or more and 2 or less.
    [Claim 12] R in the general formula (9) 101 ~ R 106 The organic electroluminescent device according to claim 9, wherein at least one of the substituents represented by the formula is an electron-withdrawing group having a Hammett substitution number σp value of 0.02 or more and 2 or less.

２．前記一般式（３）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。 2 . An organic electroluminescence device comprising a light emitting layer containing the metal complex represented by the general formula (3).

３．前記一般式（４）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。 3 . An organic electroluminescence device comprising a light emitting layer containing the metal complex represented by the general formula (4).

４．前記一般式（４）において、Ｎ−Ｍ−Ｙ−Ｚの２面角（即ち２つの環のねじれ角）が９度以上９０度未満であることを特徴とする前記３に記載の有機エレクトロルミネッセンス素子。 4 . 4. The organic electroluminescence as described in 3 above, wherein in the general formula (4), the dihedral angle of NMYZ (that is, the twist angle of the two rings) is 9 degrees or more and less than 90 degrees. element.

５．前記一般式（５）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。 5 . An organic electroluminescence device comprising a light emitting layer containing the metal complex represented by the general formula (5).

６．前記一般式（６）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。 6 . An organic electroluminescence device comprising a light emitting layer containing the metal complex represented by the general formula (6).

７．前記一般式（７）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。 7 . An organic electroluminescence device comprising a light emitting layer containing a metal complex represented by the general formula (7).

８．前記一般式（８）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。 8 . An organic electroluminescence device comprising a light emitting layer containing a metal complex represented by the general formula (8).

９．前記一般式（９）で表される金属錯体を発光層に含有することを特徴とする有機エレクトロルミネッセンス素子。 9 . An organic electroluminescence device comprising a light emitting layer containing the metal complex represented by the general formula (9).

１０．前記一般式（７）のＡｒで表される芳香族基が、ハメットの置換基定数σｐ値が０．０２以上２以下の電子吸引性基で置換された芳香族炭化水素環基であることを特徴とする前記７に記載の有機エレクトロルミネッセンス素子。 1 0 . The aromatic group represented by Ar in the general formula (7) is an aromatic hydrocarbon ring group substituted with an electron-withdrawing group having a Hammett's substituent constant σp value of 0.02 or more and 2 or less. 8. The organic electroluminescence device as described in 7 above.

１１．前記一般式（７）のＡｒで表される芳香族基が、ハメットの置換基定数σｐ値が０．０２以上２以下の電子吸引性基で置換された芳香族炭化水素環基であり、かつＲ82で表される置換基がハメットの置換規定数σｐ値が０．０２以上２以下の電子吸引性基であることを特徴とする前記７に記載の有機エレクトロルミネッセンス素子。 1 1 . The aromatic group represented by Ar in the general formula (7) is an aromatic hydrocarbon ring group substituted with an electron-withdrawing group having a Hammett's substituent constant σp value of 0.02 or more and 2 or less, and 8. The organic electroluminescence device as described in 7 above, wherein the substituent represented by R 82 is an electron-withdrawing group having a Hammett substitution prescribed number σp value of 0.02 or more and 2 or less.

１２．前記一般式（９）のＲ101〜Ｒ106で表される置換基の少なくとも１つが、ハメットの置換規定数σｐ値が０．０２以上２以下の電子吸引性基であることを特徴とする前記９に記載の有機エレクトロルミネッセンス素子。 1 2 . At least one of the substituents represented by R 101 to R 106 in the general formula (9) is an electron-withdrawing group having a Hammett substitution prescribed number σp value of 0.02 or more and 2 or less. 9. The organic electroluminescence device according to 9 .

本発明に用いられる重金属錯体は、一般式（１）、（３）〜（９）で表される。
先ず、一般式（１）で表される化合物について説明する。 The heavy metal complex used in the present invention is represented by the general formulas (1) and (3) to (9).
First, the compound represented by the general formula (1) will be described.

一般式（５）で表される金属錯体は、ビアリール配位子を構成する２つの環のうち一方がフェニル基であるものである。即ち、一般式（５）においては、該フェニル基中の他の（ヘテロ）アリール環が結合する位置の隣接位に置換基Ｒ61を有しており、該置換基は前記立体パラメータＥｓ値が−０．６以下であることが好ましい。 Metal complex represented by the general formula (5) is Ru der those one of the two rings constituting the biaryl ligands is a phenyl group. That is, in the general formula (5), the phenyl group has a substituent R 61 adjacent to the position to which another (hetero) aryl ring is bonded, and the substituent has the steric parameter Es value. It is preferably −0.6 or less.

以下に、本発明に係わる前記一般式（１）、（３）〜（９）で表される金属錯体等の具体例を示すが、本発明はこれらのみに限定されるものではない。
Hereinafter, the general formula according to the present invention (1), (3) Specific examples of such metal complex represented by - (9), the present invention is not limited thereto.

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