JP2005310733A5 - - Google Patents
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- JP2005310733A5 JP2005310733A5 JP2004162849A JP2004162849A JP2005310733A5 JP 2005310733 A5 JP2005310733 A5 JP 2005310733A5 JP 2004162849 A JP2004162849 A JP 2004162849A JP 2004162849 A JP2004162849 A JP 2004162849A JP 2005310733 A5 JP2005310733 A5 JP 2005310733A5
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(RD3、RD4はそれぞれ水素原子または置換基を表し、RD1、RD2はそれぞれ置換基を表す。nD1、nD2は0〜4の整数を表し、RD1、RD2をそれぞれ複数個有する場合、複数個のRD1、RD2は同じであっても異なってもよく、連結して環を形成してもよい。YD1は1,2位で置換したビニル基、フェニレン環、ピリジン環、ピラジン環、ピリミジン環または炭素数1〜8のメチレン基を表す。)
[24]前記一般式(X1)で表される化合物。
[25]前記一般式(X2)で表される化合物。
[26]前記一般式(X3)で表される化合物。
本発明は以下の(1)〜(21)に関するものである。
(1)
一対の電極間に発光層を含む少なくとも一層の有機層を有する有機電界発光素子であって、一対の電極間の少なくとも一層に、一般式(9)で表される化合物の少なくとも一種を含有することを特徴とする有機電界発光素子。
(2)
前記R A1 とR A2 又はR A3 とR A4 が、結合して形成している環構造が、ベンゾ縮環又はピリジン縮環である、(1)に記載の有機電界発光素子。
(3)
前記一般式(9)で表される化合物が一般式(7)で表される化合物であることを特徴とする(1)または(2)記載の有機電界発光素子。
(M 71 は白金イオンを表し、Y 71 、Y 72 、Y 73 はそれぞれ連結基または単結合を表し、Z 71 、Z 72 、Z 73 、Z 74 、Z 75 、Z 76 はそれぞれ置換または無置換の炭素原子、窒素原子を表し、Z 71 とZ 72 、Z 73 とZ 74 が連結基を介して結合し、環を形成しても良い。R 71 とR 72 およびR 73 とR 74 はそれぞれ結合して環構造を形成している。L 75 はM 71 に配位する配位子を表す。n 71 は0を表す。)
(4)
前記R 71 とR 72 又はR 73 とR 74 が、結合して形成している環構造が、ベンゾ縮環又はピリジン縮環である、(3)に記載の有機電界発光素子。
(5)
前記一般式(7)で表される化合物が一般式(11)で表される化合物であることを特徴とする(3)に記載の有機電界発光素子。
(R C1 、R C2 はそれぞれ水素原子または置換基を表し、R C3 、R C4 、R C5 、R C6 はそれぞれ置換基を表す。n C3 、n C6 は0〜3、n C4 、n C5 は0〜4の整数を表し、R C3 、R C4 、R C5 、R C6 をそれぞれ複数個有する場合、複数個のR C3 、R C4 、R C5 、R C6 は同じであっても異なってもよく、連結して環を形成してもよい。)
(6)
前記置換基が、アルキル基、アリール基、アミノ基又はアシル基である、(3)〜(5)のいずれかに記載の有機電界発光素子。
(7)
前記R C1 、R C2 が、それぞれ、アルキル基である、(5)に記載の有機電界発光素子。
(8)
一対の電極間に少なくとも一層の発光層を含む有機電界発光素子であって、正孔輸送層と発光層に加え、励起子ブロック層、正孔注入層、正孔ブロック層および電子輸送層からなる群から選ばれる少なくとも一つの層を有することを特徴とする(1〜7のいずれか一項に記載の有機電界発光素子。
(9)
一対の電極間に少なくとも一層の発光層を含む有機電界発光素子であって、発光層のホスト材料がアミン化合物、金属キレートオキシノイド化合物(金属はアルミニウム、亜鉛、または遷移金属)、ポリアリーレン化合物、縮合芳香族炭素環化合物および非錯体芳香族ヘテロ環化合物からなる群から選ばれることを特徴とする(1)〜(8)のいずれか一項に記載の有機電界発光素子。
(10)
一対の電極間に少なくとも一層の電子輸送層を含む有機電界発光素子であって、電子輸送材料が、金属キレートオキシノイド化合物、ポリアリーレン化合物、縮合芳香族炭素環化合物および非錯体芳香族ヘテロ環化合物からなる群から選ばれることを特徴とする(1)〜(9)のいずれか一項に記載の有機電界発光素子。
(11)
一対の電極間に少なくとも一層の発光層を含む有機電界発光素子であって、発光層のホスト材料が少なくとも2種の化合物からなることを特徴とする(1)〜(10)のいずれか一項に記載の有機電界発光素子。
(12) 一般式(11)で表される化合物。
(13)
前記置換基が、アルキル基、アリール基、アミノ基又はアシル基である、(12)に記載の化合物。
(14)
前記R C1 、R C2 が、それぞれ、炭素数1〜10のアルキル基である、(12)又は(13)に記載の化合物。
(15)
(1)〜(7)のいずれかに記載の前記一般式(7)、(9)又は(11)で表される発光材料。
(16)
(1)〜(7)のいずれかに記載の前記一般式(7)、(9)又は(11)で表される化合物を含有する発光層。
(17)
(1)〜(11)のいずれかに記載の有機電界発光素子を用いた表示素子。
(18)
(1)〜(11)のいずれかに記載の有機電界発光素子を用いたディスプレイ。
(19)
(1)〜(11)のいずれかに記載の有機電界発光素子を用いた照明光源。
なお、本発明は上記(1)〜(21)に関するものであるが、その他の事項についても参考のために記載した。
(R D3 and R D4 each represent a hydrogen atom or a substituent, and R D1 and R D2 each represent a substituent. N D1 and n D2 each represent an integer of 0 to 4, and R D1 and R D2 each represent a plurality of R D1 and R D2. In the case of having one, a plurality of R D1 and R D2 may be the same or different, and may be connected to form a ring, Y D1 is a vinyl group substituted at the 1- or 2-position, a phenylene ring, Represents a pyridine ring, a pyrazine ring, a pyrimidine ring or a methylene group having 1 to 8 carbon atoms.)
[24] A compound represented by the general formula (X1).
[25] A compound represented by the general formula (X2).
[26] A compound represented by the general formula (X3).
The present invention relates to the following (1) to (21).
(1)
An organic electroluminescent device having at least one organic layer including a light emitting layer between a pair of electrodes, wherein at least one of the compounds represented by the general formula (9) is contained in at least one layer between the pair of electrodes. An organic electroluminescent device characterized by the above.
(2)
The organic electroluminescent device according to (1), wherein the ring structure formed by combining R A1 and R A2 or R A3 and R A4 is a benzo condensed ring or a pyridine condensed ring.
(3)
The organic electroluminescent element according to (1) or (2), wherein the compound represented by the general formula (9) is a compound represented by the general formula (7).
(M 71 represents a platinum ion, Y 71 , Y 72 and Y 73 each represents a linking group or a single bond, and Z 71 , Z 72 , Z 73 , Z 74 , Z 75 and Z 76 are each substituted or unsubstituted. Z 71 and Z 72 , Z 73 and Z 74 may be bonded via a linking group to form a ring, and R 71 and R 72 and R 73 and R 74 are respectively Bonded to form a ring structure, L 75 represents a ligand coordinated to M 71 , and n 71 represents 0.)
(4)
The organic electroluminescence device according to (3), wherein the ring structure formed by combining R 71 and R 72 or R 73 and R 74 is a benzo-fused ring or a pyridine-fused ring.
(5)
The organic electroluminescent element as described in (3), wherein the compound represented by the general formula (7) is a compound represented by the general formula (11).
(R C1 and R C2 each represent a hydrogen atom or a substituent, and R C3 , R C4 , R C5 and R C6 each represent a substituent. N C3 and n C6 represent 0 to 3, n C4 and n C5 represent represents an integer of 0 to 4, when having a plurality of R C3, R C4, R C5 , R C6 , respectively, the plurality of R C3, R C4, R C5 , R C6 may be the same or different , May be linked to form a ring.)
(6)
The organic electroluminescent element according to any one of (3) to (5), wherein the substituent is an alkyl group, an aryl group, an amino group, or an acyl group.
(7)
The organic electroluminescence device according to (5), wherein R C1 and R C2 are each an alkyl group.
(8)
An organic electroluminescent device comprising at least one light emitting layer between a pair of electrodes, comprising an exciton block layer, a hole injection layer, a hole block layer and an electron transport layer in addition to a hole transport layer and a light emitting layer It has at least 1 layer chosen from a group (The organic electroluminescent element as described in any one of 1-7 characterized by the above-mentioned.
(9)
An organic electroluminescent element including at least one light emitting layer between a pair of electrodes, wherein a host material of the light emitting layer is an amine compound, a metal chelate oxinoid compound (a metal is aluminum, zinc, or a transition metal), a polyarylene compound, The organic electroluminescence device according to any one of (1) to (8), wherein the organic electroluminescence device is selected from the group consisting of a condensed aromatic carbocyclic compound and a non-complex aromatic heterocyclic compound.
(10)
An organic electroluminescent device comprising at least one electron transport layer between a pair of electrodes, wherein the electron transport material is a metal chelate oxinoid compound, a polyarylene compound, a condensed aromatic carbocyclic compound, and a non-complex aromatic heterocyclic compound The organic electroluminescent element according to any one of (1) to (9), wherein the organic electroluminescent element is selected from the group consisting of:
(11)
An organic electroluminescent element including at least one light emitting layer between a pair of electrodes, wherein the host material of the light emitting layer is composed of at least two kinds of compounds. The organic electroluminescent element of description.
(12) A compound represented by the general formula (11).
(13)
The compound according to (12), wherein the substituent is an alkyl group, an aryl group, an amino group, or an acyl group.
(14)
The compound according to (12) or (13), wherein each of R C1 and R C2 is an alkyl group having 1 to 10 carbon atoms.
(15)
The luminescent material represented by the general formula (7), (9) or (11) according to any one of (1) to (7).
(16)
(1) The light emitting layer containing the compound represented by the said General formula (7) in any one of (7), (9) or (11).
(17)
(1) The display element using the organic electroluminescent element in any one of (11).
(18)
A display using the organic electroluminescent element according to any one of (1) to (11).
(19)
(1) The illumination light source using the organic electroluminescent element in any one of (11).
In addition, although this invention is related to said (1)-(21), the other matter was also described for reference.
以下に本発明の具体的実施例を述べるが、本発明の実施の態様はこれらに限定されない。
なお、本実施例において化合物(1)、(15)、(88)を用いた実施例は参考例と読み替えるものとする。
・化合物(1)の合成
6,6’−ビス(2−ヒドロキシフェニル)−2,2’−ビピリジル0.1g、PtCl2 0.16gにベンゾニトリル10mlを加え、窒素雰囲気下3時間加熱還流させた。反応液を室温に冷却し、メタノールを加え沈殿させ、吸引ろ過した。得られた固体をシリカゲルカラムクロマトグラフィー(展開溶媒クロロホルム)で精製し、化合物(1)0.06gを得た。マススペクトル測定により化合物(1)の構造を確認した。窒素雰囲気下、化合物(1)を含むクロロホルム溶液にUV光を照射したところ、赤橙色の発光(λmax=624nm)が得られた。
Specific examples of the present invention will be described below, but the embodiments of the present invention are not limited thereto.
In this example, examples using compounds (1), (15), and (88) should be read as reference examples.
・ Synthesis of Compound (1) Add 10 ml of benzonitrile to 0.16 g of 6,6′-bis (2-hydroxyphenyl) -2,2′-bipyridyl and 0.16 g of PtCl 2, and heat to reflux for 3 hours in a nitrogen atmosphere. It was. The reaction solution was cooled to room temperature, methanol was added for precipitation, and suction filtration was performed. The obtained solid was purified by silica gel column chromatography (developing solvent chloroform) to obtain 0.06 g of Compound (1). The structure of the compound (1) was confirmed by mass spectrum measurement. When a chloroform solution containing the compound (1) was irradiated with UV light in a nitrogen atmosphere, reddish orange light emission (λ max = 624 nm) was obtained.
Claims (19)
(MA1 は白金イオンを表し、QA1、QA2はそれぞれ含窒素ヘテロ環を形成する原子群を表す。R A1 とR A2 およびR A3 とR A4 はそれぞれ結合して環構造を形成している。YA2、YA3はそれぞれ連結基または単結合を表す。YA1はかっこ内の2つの2座配位子をそれぞれ連結する連結基、単結合、または二重結合を表す。LA5はMA1に配位する配位子を表す。nA1は0を表す。) An organic electroluminescent device having at least one organic layer including a light emitting layer between a pair of electrodes, wherein at least one of the compounds represented by the general formula (9) is contained in at least one layer between the pair of electrodes. An organic electroluminescent element characterized by the above.
(M A1 represents a platinum ion-, Q A1, Q A2 each represent an atomic group forming a nitrogen-containing hetero ring. R A1 and R A2 and R A3 and R A4 are each bonded to form a ring structure and are. Y A2, Y A3 .L representative of each represents a linking group or a single bond .Y A1 linking group connecting each two bidentate ligand in parentheses, a single bond, or a double bond A5 Represents a ligand coordinated to M A1, and n A1 represents 0. )
(M(M 7171 は白金イオンを表し、YRepresents platinum ion, Y 7171 、Y, Y 7272 、Y, Y 7373 はそれぞれ連結基または単結合を表し、ZEach represents a linking group or a single bond; 7171 、Z, Z 7272 、Z, Z 7373 、Z, Z 7474 、Z, Z 7575 、Z, Z 7676 はそれぞれ置換または無置換の炭素原子、窒素原子を表し、ZEach represents a substituted or unsubstituted carbon atom or nitrogen atom; 7171 とZAnd Z 7272 、Z, Z 7373 とZAnd Z 7474 が連結基を介して結合し、環を形成しても良い。RMay be bonded via a linking group to form a ring. R 7171 とRAnd R 7272 およびRAnd R 7373 とRAnd R 7474 はそれぞれ結合して環構造を形成している。LAre bonded to each other to form a ring structure. L 7575 はMIs M 7171 に配位する配位子を表す。nRepresents a ligand coordinated to n 7171 は0を表す。)Represents 0. )
(R(R C1C1 、R, R C2C2 はそれぞれ水素原子または置換基を表し、REach represents a hydrogen atom or a substituent, and R C3C3 、R, R C4C4 、R, R C5C5 、R, R C6C6 はそれぞれ置換基を表す。nEach represents a substituent. n C3C3 、n, N C6C6 は0〜3、n0-3, n C4C4 、n, N C5C5 は0〜4の整数を表し、RRepresents an integer of 0 to 4 and R C3C3 、R, R C4C4 、R, R C5C5 、R, R C6C6 をそれぞれ複数個有する場合、複数個のREach having a plurality of R, a plurality of R C3C3 、R, R C4C4 、R, R C5C5 、R, R C6C6 は同じであっても異なってもよく、連結して環を形成してもよい。)May be the same or different and may be linked to form a ring. )
(RC1、RC2はそれぞれ水素原子または置換基を表し、RC3、RC4、RC5、RC6はそれぞれ置換基を表す。nC3、nC6は0〜3、nC4、nC5は0〜4の整数を表し、RC3、RC4、RC5、RC6をそれぞれ複数個有する場合、複数個のRC3、RC4、RC5、RC6は同じであっても異なってもよく、連結して環を形成してもよい。) The compound represented by General formula (11).
(R C1 and R C2 each represent a hydrogen atom or a substituent, and R C3 , R C4 , R C5 and R C6 each represent a substituent. N C3 and n C6 represent 0 to 3, n C4 and n C5 represent represents an integer of 0 to 4, when having a plurality of R C3, R C4, R C5 , R C6 , respectively, the plurality of R C3, R C4, R C5 , R C6 may be the same or different , May be linked to form a ring.)
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