JP4290858B2 - Organic electroluminescence device - Google Patents

Organic electroluminescence device Download PDF

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JP4290858B2
JP4290858B2 JP2000175981A JP2000175981A JP4290858B2 JP 4290858 B2 JP4290858 B2 JP 4290858B2 JP 2000175981 A JP2000175981 A JP 2000175981A JP 2000175981 A JP2000175981 A JP 2000175981A JP 4290858 B2 JP4290858 B2 JP 4290858B2
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JP2001357977A (en
Inventor
雅之 三島
俊大 伊勢
久 岡田
敏樹 田口
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富士フイルム株式会社
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Description

[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a light emitting device, and particularly to an organic electroluminescent device having high luminance, high luminous efficiency, and excellent durability.
[0002]
[Prior art]
Today, research and development on various light emitting elements are active, and among them, an organic electroluminescence (EL) element is attracting attention as a promising light emitting element because it can emit light with high luminance at a low voltage. For example, a light-emitting element that forms an organic thin film by vapor deposition of an organic compound is known (Applied Physics Letters, 51, 913, 1987). The light-emitting element described in this document uses tris (8-hydroxyquinolinato) aluminum complex (Alq) as an electron transport material, and is laminated with a hole transport material (amine compound), thereby making it a conventional single-layer element. Compared to this, the emission characteristics are greatly improved.
[0003]
In recent years, application of organic EL elements to color displays has been actively studied, but in order to develop high-performance color displays, it is necessary to improve the characteristics of blue, green, and red light-emitting elements. .
Iridium complex (Ir (ppy))Three) Has been reported (Applied Physics Letters 75, 4 (1999)). This device has reached an external quantum yield of 8%, which exceeds the external quantum yield of 5%, which is said to be the limit of the conventional device, but has a problem in durability, and an improvement thereof has been desired.
[0004]
On the other hand, organic light-emitting elements that achieve high-intensity light emission are elements in which organic substances are stacked by vacuum vapor deposition, but depending on the application method from the viewpoint of simplification of the manufacturing process, processability, large area, etc. Device fabrication is desirable. However, the device manufactured by the conventional coating method is inferior to the device manufactured by the vapor deposition method in terms of light emission luminance and light emission efficiency, and high luminance and high efficiency light emission have been a major issue.
[0005]
[Problems to be solved by the invention]
The present invention has been made in view of the above circumstances, and it is an object of the present invention to provide an organic electroluminescent device capable of emitting light with high luminance and high efficiency and having excellent durability.
[0006]
[Means for Solving the Problems]
This problem has been achieved by the light emitting device described below.
(1) In a light-emitting element in which an organic light-emitting layer or an organic compound layer including an organic light-emitting layer is formed between a pair of electrodes provided on a substrate, the organic light-emitting layer has a condensed heterocyclic skeleton having a nitrogen atom in a condensation portion. An aromatic heterocycle having at least one nitrogen atom at a position that is not a condensed part in the heteroaromatic ringIs the imidazopyridine ringA compound represented by the following general formula (1):Orthoiridium complex represented by the following general formula (7)An organic electroluminescent device comprising:
General formula (1)
[0007]
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[0008]
  In the formula, X represents a carbon atom or a nitrogen atom. Z1And Z2Each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.
Embedded image
(Wherein R 31 , R 32 Represents a substituent. q 31 , Q 32 Represents an integer of 0 to 4, q 31 + Q 32 Is 1 or more. q 31 , Q 32 If R is 2 or more, multiple R 31 , R 32 May be the same or different from each other. n 3 Is an integer from 0 to 5, m 3 Represents 1, 2 or 3. L 3 Represents a ligand. )
(2The organic electroluminescent device according to (1), wherein the compound represented by the general formula (1) is selected from the following compounds.
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[Chemical 2-5]
(3) The compound represented by the general formula (1) is represented by the formula HT-6, HT-7, HT-9, HT-12., AndAnd HT-17 (2) Organic electroluminescent device as described.
[0009]
BEST MODE FOR CARRYING OUT THE INVENTION]
[0010]
  Heterogeneous boneThe case isMidazopilisiInis there.
[0011]
  In general formula (1)Z1And Z2Becomes a cyclic structure and forms a condensed heterocycle as shown above, and this condensed heterocycle can be substituted with various substituents in addition to a hydrogen atom. For example, for example, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), a cyano group, a formyl group, or a substituted or unsubstituted alkyl group (preferably having 1 to 30 carbon atoms, more preferably Has 1 to 15 carbon atoms, for example, a methyl group, a t-butyl group, a cyclohexyl group, and the like, and an alkenyl group (preferably 2 to 30 carbon atoms, more preferably 2 to 15 carbon atoms). For example, vinyl group, 1-propenyl group, 1-buten-2-yl group, cyclohexen-1-yl group, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 2 carbon atoms). 15. For example, ethynyl group, 1-propynyl group, etc.), aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms. For example, phenyl group, tolyl group, xylyl group) , Naphthyl group, biphenylyl group, a pyrenyl group.)
[0012]
Heterocyclic group (preferably a 5- or 6-membered ring, which may be condensed with another ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom. Preferably, the carbon number is 2 to 30, More preferably, it has 2 to 15 carbon atoms, for example, pyridyl group, piperidyl group, oxazolyl group, oxadiazolyl group, tetrahydrofuryl group, carbazolyl group, thienyl group, etc.), primary to tertiary amino group (amino group) , An alkylamino group, an arylamino group, a dialkylamino group, a diarylamino group, an alkylarylamino group, a heterocyclic amino group, a bisheterocyclic amino group, etc., preferably a tertiary amino group, more preferably 1-30 carbon atoms. Is a carbon number of 1 to 16. Examples include a dimethylamino group, a diphenylamino group, and a phenylnaphthylamino group. Imino group (-CR11= NR12Or -N = CR13R14A group represented by Where R11~ R14Is a group selected from a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an acyl group, and a primary to tertiary amino group. Preferably it is C1-C30, More preferably, it is C1-C15. ), An alkoxy group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 15. Examples thereof include a methoxy group, an ethoxy group, and a cyclohexyloxy group).
[0013]
An aryloxy group (including a heteroaryloxy group. Preferably it has 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms. Examples thereof include a phenoxy group, a 1-naphthoxy group, and a 4-phenylphenoxy group. ), An alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms. Examples thereof include a methylthio group, an ethylthio group, a cyclohexylthio group, etc.), an arylthio group (also a heteroarylthio group). Preferably, it has 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms, for example, phenylthio group, tolylthio group, etc., carbonamide group (preferably 1 to 30 carbon atoms, more preferably A carbon number of 1 to 15. Examples thereof include an acetamido group, a benzoylamide group, and an N-methylbenzoylamide group. Preferably it has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, such as methanesulfonamide group, benzenesulfonamide group, p-toluenesulfonamide group, etc.), carbamoyl group (preferably carbon 1 to 30 and more preferably 1 to 15. Examples thereof include an unsubstituted carbamoyl group, a methylcarbamoyl group, a dimethylcarbamoyl group, a phenylcarbamoyl group, a diphenylcarbamoyl group, and a dioctylcarbamoyl group. Sulfamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms. For example, unsubstituted sulfamoyl group, methylsulfamoyl group, dimethylsulfamoyl group, phenylsulfamoyl group, diphenylsulfamoyl group Famoyl group, dioctylsulfamoyl group, etc.), al A kill carbonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms).
[0014]
For example, an acetyl group, a propionyl group, a butyroyl group, a lauroyl group, etc. are mentioned. ), An arylcarbonyl group (including a heteroarylcarbonyl group. Preferably, it has 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms. Examples thereof include a benzoyl group and a naphthoyl group), an alkylsulfonyl group ( The number of carbon atoms is preferably 1 to 30, more preferably 1 to 15. For example, a methanesulfonyl group, an ethanesulfonyl group, and the like are included, and an arylsulfonyl group (including a heteroarylsulfonyl group). 6-30, more preferably 6-15 carbon atoms, for example, benzenesulfonyl group, p-toluenesulfonyl group, 1-naphthalenesulfonyl group, etc.), alkoxycarbonyl group (preferably 1-30 carbon atoms). More preferably, it has 1 to 15 carbon atoms, for example, methoxycarbonyl group, ethoxycarbonyl group, butoxycarbo An aryloxycarbonyl group (including a heteroaryloxycarbonyl group, preferably 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms), for example, phenoxycarbonyl group, 1-naphthoxy A carbonyl group, etc.), an alkylcarbonyloxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, such as an acetoxy group, a propionyloxy group, a butyroyloxy group, etc.). An arylcarbonyloxy group (including a heteroarylcarbonyloxy group, preferably having 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms, such as a benzoyloxy group and a 1-naphthoyloxy group). A urethane group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms. A bonamide group, a phenoxycarbonamide group, a methylaminocarbonamide group, etc.), a ureido group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 15. For example, a methylaminocarbonamide group, Dimethylaminocarbonamide group, diphenylaminocarbonamide group, etc.), carbonate group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms. For example, methoxycarbonyloxy group, phenoxycarbonyl An oxy group, etc.).
[0015]
Furthermore, the heterocyclic compound represented by the general formula (1) may form a polymer compound having the structure in one part of the repeating unit. In this case, Z1, Z2Contains a polymerizable group such as an ethylenically unsaturated bond or a polymerizable group such as a carboxyl group, amino group or ester group that causes condensation polymerization, and the group is polymerized to form a polymer. Alternatively, the precursor of the heterocyclic compound represented by the general formula (1) may form a polymer while forming the heterocyclic skeleton of the general formula (1).
As for the heterocyclic compound represented by the general formula (1), it is possible to use a compound having a structure that finally expresses a function as it is, regardless of whether it is a low molecule or a polymer. Precursors may be used in organic electroluminescent devices and may be induced into the final structure by physical or chemical post-treatment after the device is constructed or in the process. When used as a low molecular weight compound, the molecular weight is preferably in the range of 200 to 5000, preferably 300 to 2000. When used as a polymer compound, the molecular weight (Mw) is preferably in the range of 2000 to 100000, preferably 5000 to 100,000.
[0016]
  The heterocyclic compound represented by the general formula (1) can be synthesized by a known method. Hereinafter, a method for synthesizing a specific compound and a part thereof will be disclosed. Of course, the present invention is not limited by this specific example. The following compounds HT-1 to HT-4, HT-10, HT-11~ 16, HT-19 to HT-22, HT-24, and HT-25 are reference compounds.
[0017]
[Chemical 3]
[0018]
[Formula 4]
[0019]
[Chemical formula 5]
[0020]
[Chemical 6]
[0021]
[Chemical 7]
[0022]
[Chemical 8]
[0023]
[Chemical 9]
[0024]
[Chemical Formula 10]
[0025]
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[0026]
(Synthesis of Compound HT-1)
A three-necked flask with a volume of 300 ml is charged with 10.8 g (115 mmol) of α-picoline and 20 ml of benzene and refluxed with stirring. A solution prepared by dissolving 23.8 g (117 mmol) of phenacyl bromide in 50 ml of benzene is added dropwise thereto. After completion of the dropwise addition, the solution becomes cloudy and crystal precipitation begins. Continue heating to reflux for an additional 4 hours. After cooling, the precipitated crystals are filtered off and dried. The crystals are charged into a three-necked flask having a volume of 2 liters, and 300 ml of water is added thereto, and the internal temperature is raised to 80 ° C. with vigorous stirring. When 84 g (1.0 mol) of sodium hydrogen carbonate is gradually added thereto, the color of the solution turns yellow while vigorously foaming. Crystals begin to precipitate after a while, and stirring is continued for 30 minutes. After cooling, the crystals were filtered off and washed with water, and then the crude crystals were recrystallized from a mixed solvent of acetonitrile / water to obtain 14 g of compound HT-1.
[0027]
(Synthesis of Compound HT-5)
A 2-liter eggplant-shaped flask is charged with 58 g (0.6 mol) of 2-aminopyridine, 100 g (0.5 mol) of phenacyl bromide, 84 g (1.0 mol) of sodium bicarbonate, and 600 ml of ethanol, and stirred at room temperature for 2 hours. Then, the mixture is heated to reflux for 2 hours. After standing to cool, it is poured into 3 liters of cold water, and the precipitated crystals are filtered off. The crude crystals were washed with cold water and recrystallized from 60 mol% ethanol to obtain 80 g of compound HT-5 crystals.
[0028]
Next, the orthometalated metal complex used in the present invention will be described. Orthometalated metal complexes include, for example, “Organic Metal Chemistry: Fundamentals and Applications” p150, 232 Akio Yamamoto, 1982, “Photochemistry and Photophysics of Coordination Compounds” p71-p77, p135-p146 Springer- This is a general term for compound groups described in Verlag H. Yersin's 1987 issue. As the central metal of the metal complex, any transition metal can be used. In the present invention, rhodium, platinum, gold, iridium, ruthenium, palladium and the like can be preferably used. Of these, iridium is particularly preferred.
[0029]
The metal valence of the orthometalated metal complex is not particularly limited, but trivalent is preferable when iridium is used. The ligand of the orthometalated metal complex is not particularly limited as long as it can form an orthometalated metal complex. For example, an aryl group-substituted nitrogen-containing heterocyclic derivative (the aryl group is substituted at the nitrogen-containing heterocyclic ring). On the carbon adjacent to the nitrogen atom, examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, and a pyrenyl group. Examples of the nitrogen-containing heterocycle include pyridine, pyrimidine, pyrazine, pyridazine, quinoline, and isoquinoline. Quinoxaline, phthalazine, quinazoline, naphtholidine, cinnoline, perimidine, phenanthroline, pyrrole, imidazole, pyrazole, oxazole, oxadiazole, triazole, thiadiazole, benzimidazole, benzoxazole, benzthiazole, phenanthridine, etc. A heteroaryl group-substituted nitrogen-containing heterocyclic derivative (the position of substitution of the heteroaryl group is on the adjacent carbon of the nitrogen-containing heterocyclic nitrogen atom, and examples of the heteroaryl group include the nitrogen-containing heterocyclic derivatives described above. Group, thiophenyl group, furyl group, etc.), 7,8-benzoquinoline derivative, phosphinoaryl derivative, phosphinoheteroaryl derivative, phosphinoxyaryl derivative, phosphinoxyheteroaryl derivative, aminomethylaryl derivative, Examples include aminomethyl heteroaryl derivatives. Preferred are aryl group-substituted nitrogen-containing aromatic heterocyclic derivatives, heteroaryl group-substituted nitrogen-containing aromatic heterocyclic derivatives, and 7,8-benzoquinoline derivatives, and phenylpyridine derivatives, thiophenylpyridine derivatives, and 7,8-benzoquinoline derivatives. Further preferred are thiophenylpyridine derivatives and 7,8-benzoquinoline derivatives.
[0030]
The compound of the present invention may have other ligands in addition to the ligands necessary for forming the orthometalated metal complex. There are various known ligands as other ligands. For example, “Photochemistry and Photophysics of Coordination Compounds” published by Springer-Verlag H. Yersin in 1987, “Organic Metal Chemistry-Fundamentals and Applications”裳 華 房 社 By Akio Yamamoto Published in 1982 and the like, preferably a halogen ligand (preferably a chlorine ligand), a nitrogen-containing heterocyclic ligand (for example, bipyridyl, phenanthroline, etc.) ), A diketone ligand, more preferably a chlorine ligand or a bipyridyl ligand.
[0031]
The orthometalated metal complex of the present invention may have one type of ligand or a plurality of types. The number of ligands in the complex is preferably 1 to 3, more preferably 1, 2 and even more preferably 1.
[0032]
The number of carbon atoms of the orthometalated metal complex of the present invention is preferably 5 to 100, more preferably 10 to 80, and still more preferably 14 to 50.
[0033]
A preferred form of the orthometalated metal complex of the present invention is a compound having a partial structure represented by the following general formula (2) or a tautomer thereof, a compound having a partial structure represented by the general formula (3) or A tautomer thereof, a compound having a partial structure represented by the general formula (4), or a tautomer thereof. Among these, a compound having a partial structure represented by the general formula (2) or a tautomer thereof, or a compound having a partial structure represented by the general formula (3) or a tautomer thereof is preferable.
[0034]
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[0035]
The compound having a partial structure represented by the general formula (2) or a tautomer thereof may have one iridium atom in the compound, or may be a so-called dinuclear complex having two or more. good. Other metal atoms may be contained at the same time. The same applies to the compound having a partial structure represented by the general formula (3) or the general formula (4) or a tautomer thereof.
[0036]
R in the general formula (4)1, R2Represents a substituent. q1, Q2Represents an integer of 0 to 4 and q1+ Q2Is 1 or more. q1, Q2If R is 2 or more, multiple R1, R2May be the same or different from each other.
[0037]
R1, R2As, for example, an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, n -Octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 carbon atoms). For example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 carbon atoms). For example, propargyl, 3-pentynyl, etc.), an aryl group (preferably having 6 to 3 carbon atoms) , More preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, including, for example, phenyl, p-methylphenyl, naphthyl, anthranyl, etc.), amino group (preferably having 0 to 30 carbon atoms, More preferably, it has 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, and examples thereof include amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino and the like, and an alkoxy group (preferably). Has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy and the like, and aryloxy groups ( Preferably it has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 carbon atoms. Is 12, for example phenyloxy, 1-naphthyloxy, 2-naphthyloxy.),
[0038]
A heteroaryloxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), acyl A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group (preferably Has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl, ethoxycarbonyl and the like, and an aryloxycarbonyl group (preferably 7 carbon atoms). To 30, more preferably 7 to 20, and particularly preferably carbon number -12, such as phenyloxycarbonyl), acyloxy groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy, Benzoyloxy, etc.), an acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino. ), An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino), aryloxycarbonyl An amino group (preferably having a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, Preferably 7 to 12 carbon atoms, e.g., phenyloxycarbonylamino and the like.),
[0039]
A sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino), a sulfamoyl group ( Preferably it is C0-30, More preferably, it is C0-20, Most preferably, it is C0-12, for example, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl etc. are mentioned. ), A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl and the like.) An alkylthio group (preferably having 1 to 30 carbon atoms) Preferably it is C1-C20, Most preferably, it is C1-C12, for example, methylthio, ethylthio etc. are mentioned, for example, An arylthio group (Preferably C6-C30, More preferably C6-C20, Particularly preferably, it has 6 to 12 carbon atoms, and examples thereof include phenylthio, etc.), a heteroarylthio group (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms). For example, pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, and a sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 carbon atom). -20, particularly preferably 1 to 12 carbon atoms, such as mesyl, tosyl, etc.), sulfinyl group (preferably From 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methane sulfinyl, and the like benzenesulfinyl.),
[0040]
Ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include ureido, methylureido, phenylureido), phosphoric acid amide group (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide), hydroxy group, mercapto Group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group (preferably It has 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms. Examples of the hetero atom include a nitrogen atom and an oxygen atom. Sulfur atom, specifically, for example, imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, etc., silyl group (preferably having 3 to 40 carbon atoms). Preferably, it has 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl. These substituents may be further substituted. R1Group, R2Groups or R1Group and R2A group may be bonded to form a condensed ring structure.
[0041]
R1, R2Is preferably an alkyl group, an aryl group, an alkoxy group, or a group that is bonded to form a condensed ring structure, and more preferably an alkyl group or a group that is bonded to form an aromatic condensed ring structure. q1, Q2Is preferably 0, 1, 2 and more preferably q1+ Q2= 1 or 2.
[0042]
OhFurther preferred forms of the metallized metal complex are a compound represented by the general formula (5), a compound represented by the general formula (6), and a compound represented by the general formula (7)..
[0043]
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[0044]
The general formula (5) will be described. R11, R12Represents a substituent, and the substituent is R1And the substituents described in the above.
R11, R12Is preferably an alkyl group or an aryl group, more preferably an alkyl group.
q11Represents an integer of 0 to 2, 0 and 1 are preferable, and 0 is more preferable. q12Represents an integer of 0 to 4, preferably 0 or 1, and more preferably 0. q11, Q12If R is 2 or more, multiple R11, R12May be the same or different from each other, and may be connected to form a condensed ring.
[0045]
L1Represents a ligand. Examples of the ligand include the ligands necessary for forming the orthometalated iridium complex and the ligands described in the other ligands. L1Is preferably a ligand necessary for forming an orthometalated iridium complex, a nitrogen-containing heterocyclic ligand, a diketone ligand, or a halogen ligand, and more preferably required for forming an orthometalated iridium complex. Ligand, bipyridyl ligand.
n1Represents an integer of 0 to 5, with 0 being preferred. m1Represents 1, 2 or 3, preferably 3. n1, M1The combination of numbers is preferably a combination of numbers in which the metal complex represented by the general formula (5) becomes a neutral complex.
[0046]
The general formula (6) will be described. Rtwenty one, N2, M2, L2Are the R11, N1, M1, L1Are synonymous with each other. qtwenty oneRepresents an integer of 0 to 8, preferably 0. qtwenty oneWhen is 2 or more, a plurality of Rtwenty oneMay be the same or different from each other, and may be linked to form a condensed ring.
The general formula (7) will be described. R31, R32, Q31, Q32, NThree, MThree, LThreeAre the R1, R2, Q1, Q2, N1, M1, L1Are synonymous with each other.
[0047]
The ortho-metalated metal complex of the present invention may be a so-called low molecular compound having one repeating unit such as the general formula (2), or a so-called oligomer having a plurality of repeating units such as the general formula (2). A compound or a polymer compound (average molecular weight (Mw: polystyrene conversion) is preferably 1000 to 5000000, more preferably 2000 to 100000, and still more preferably 3000 to 100,000). The compound of the present invention is preferably a low molecular compound.
[0048]
Next, although the compound example used for this invention is shown, this invention is not limited to this.
[0049]
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[0050]
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[0051]
Inorg. Chem. 1991, 30, page 1685, 1988, 27, page 3464., 1994, 33, page 545. Inorg. Chim. Acta 1991, 181 245, J. Organomet. Chem. 1987, 335, 293. J. Am. Chem. Soc. 1985, 107, 1431.
The use ratio of the “compound having a condensed heterocyclic skeleton” and the “orthometalated complex” in the organic light-emitting layer is a mass ratio, preferably 10,000: 1 to 1: 10000, more preferably 1000: 1 to 1: 10. In addition, the amount of each of the “compound having a condensed heterocyclic skeleton” and the “orthomethylated complex” in the organic light emitting layer is preferably 1 to 100% by mass, more preferably 10 to 100% by mass.
The thickness of the organic light emitting layer is preferably 0.001 to 10,000 nm, more preferably 0.01 to 1000 nm. The number of layers is preferably 1 to 100, more preferably 1 to 10.
Next, a light emitting device containing the compound of the present invention will be described. The method for forming the organic layer of the light emitting device containing the compound of the present invention is not particularly limited, but resistance heating vapor deposition, electron beam, sputtering, molecular lamination method, coating method, printing method, LB method, ink jet method. Such methods are used, and resistance heating vapor deposition and coating methods are preferable in terms of characteristics and production.
[0052]
The light-emitting device of the present invention is a device in which a plurality of organic compound thin films including a light-emitting layer or a light-emitting layer are formed between a pair of anode and cathode electrodes. In addition to the light-emitting layer, a hole injection layer, a hole transport layer, and an electron injection It may have a layer, an electron transport layer, a protective layer, etc., and each of these layers may have other functions. Various materials can be used for forming each layer.
Regarding the constituent layers of the light-emitting element and the materials used there, each document cited in “Prior Art” is representative, except for the points specified in the present invention, usually referring to these descriptions, Can be implemented.
[0053]
The anode supplies holes to a hole injection layer, a hole transport layer, a light emitting layer, and the like, and a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Is a material having a work function of 4 eV or more. Specific examples include conductive metal oxides such as tin oxide, zinc oxide, indium oxide and indium tin oxide (ITO), metals such as gold, silver, chromium and nickel, and these metals and conductive metal oxides. Inorganic conductive materials such as copper iodide and copper sulfide, organic conductive materials such as polyaniline, polythiophene, and polypyrrole, and laminates of these with ITO, preferably conductive metals It is an oxide, and ITO is particularly preferable from the viewpoint of productivity, high conductivity, transparency, and the like. Although the film thickness of the anode can be appropriately selected depending on the material, it is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, still more preferably 100 nm to 500 nm.
[0054]
As the anode, a layer formed on a soda-lime glass, non-alkali glass, a transparent resin substrate or the like is usually used. When glass is used, it is preferable to use non-alkali glass as the material in order to reduce ions eluted from the glass. Moreover, when using soda-lime glass, it is preferable to use what gave barrier coatings, such as a silica. The thickness of the substrate is not particularly limited as long as it is sufficient to maintain the mechanical strength, but when glass is used, a thickness of 0.2 mm or more, preferably 0.7 mm or more is usually used. Various methods are used for producing the anode depending on the material. For example, in the case of ITO, an electron beam method, a sputtering method, a resistance heating vapor deposition method, a chemical reaction method (such as a sol-gel method), an indium tin oxide dispersion A film is formed by a method such as coating. The anode can be subjected to cleaning or other treatments to lower the drive voltage of the element or increase the light emission efficiency. For example, in the case of ITO, UV-ozone treatment, plasma treatment, etc. are effective.
[0055]
The cathode supplies electrons to the electron injection layer, the electron transport layer, the light emitting layer, etc., and the adhesion, ionization potential, stability, etc., between the negative electrode and the adjacent layer such as the electron injection layer, electron transport layer, light emitting layer, etc. Selected in consideration of As the cathode material, a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Specific examples include alkali metals (for example, Li, Na, K, Cs, etc.) and Its fluoride, alkaline earth metal (eg Mg, Ca, etc.) and its fluoride, gold, silver, lead, aluminum, sodium-potassium alloy or mixed metal thereof, lithium-aluminum alloy or mixed metal thereof, magnesium- Examples thereof include silver alloys or mixed metals thereof, rare earth metals such as indium and ytterbium, preferably materials having a work function of 4 eV or less, more preferably aluminum, lithium-aluminum alloys or mixed metals thereof, magnesium-silver. An alloy or a mixed metal thereof. The cathode can take not only a single layer structure of the compound and the mixture but also a laminated structure including the compound and the mixture. The film thickness of the cathode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, still more preferably 100 nm to 1 μm. For production of the cathode, methods such as an electron beam method, a sputtering method, a resistance heating vapor deposition method, and a coating method are used, and a metal can be vapor-deposited alone or two or more components can be vapor-deposited simultaneously. Furthermore, a plurality of metals can be vapor-deposited simultaneously to form an alloy electrode, or a previously prepared alloy may be vapor-deposited. The sheet resistance of the anode and the cathode is preferably low, and is preferably several hundred Ω / □ or less.
[0056]
The material of the light emitting layer is a function that can inject holes from the anode or hole injection layer, hole transport layer and cathode or electron injection layer, electron transport layer when an electric field is applied, Any layer can be used as long as it can form a layer having a function of moving injected charges and a function of emitting light by providing a recombination field of holes and electrons. The light emitting layer preferably contains the amine compound of the present invention, but other light emitting materials can also be used. For example, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, perylene derivatives, perinone derivatives, oxadiazole derivatives, aldazine derivatives , Pyraziridine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styrylamine derivatives, aromatic dimethylidin compounds, 8-quinolinol derivatives, metal complexes and rare earth complexes Representative metal complexes, polymer compounds such as polythiophene, polyphenylene, polyphenylene vinylene, etc. And the like. Although the film thickness of a light emitting layer is not specifically limited, Usually, the thing of the range of 1 nm-5 micrometers is preferable, More preferably, it is 5 nm-1 micrometer, More preferably, it is 10 nm-500 nm.
The formation method of the light emitting layer is not particularly limited, but resistance heating vapor deposition, electron beam, sputtering, molecular lamination method, coating method (spin coating method, casting method, dip coating method, etc.), printing method, LB method A method such as an ink jet method is used, and a resistance heating vapor deposition method and a coating method are preferable.
[0057]
The material of the hole injection layer and the hole transport layer may be any one having a function of injecting holes from the anode, a function of transporting holes, or a function of blocking electrons injected from the cathode. Good. Specific examples include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives. , Fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole) derivatives, aniline compounds Examples thereof include conductive polymer oligomers such as copolymers, thiophene oligomers, and polythiophenes. The film thicknesses of the hole injection layer and the hole transport layer are not particularly limited, but are usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 500 nm. . The hole injection layer and the hole transport layer may have a single-layer structure composed of one or more of the materials described above, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
As a method for forming the hole injection layer and the hole transport layer, a vacuum deposition method, an LB method, an ink jet method, a method in which the hole injection / transport agent is dissolved or dispersed in a solvent (a spin coating method, a cast method, A dip coating method or the like is used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, and poly (N -Vinyl carbazole), hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, and the like.
[0058]
The material for the electron injection layer and the electron transport layer may be any material having any one of a function of injecting electrons from the cathode, a function of transporting electrons, and a function of blocking holes injected from the anode. Specific examples thereof include triazole derivatives, oxazole derivatives, oxadiazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbidiimide derivatives, fluorenylidenemethane derivatives, Various metal complexes typified by metal complexes of styrylpyrazine derivatives, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanine derivatives, 8-quinolinol derivatives, metal phthalocyanines, benzoxazole and benzothiazole ligands Etc. Although the film thickness of an electron injection layer and an electron carrying layer is not specifically limited, The thing of the range of 1 nm-5 micrometers is preferable normally, More preferably, it is 5 nm-1 micrometer, More preferably, it is 10 nm-500 nm. The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
As a method for forming the electron injection layer and the electron transport layer, a vacuum deposition method, an LB method, an ink jet method, a method in which the electron injection transport agent is dissolved or dispersed in a solvent (a spin coating method, a casting method, a dip coating method). Etc.) are used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. As the resin component, for example, those exemplified in the case of the hole injection transport layer can be applied.
[0059]
As a material for the protective layer, any material may be used as long as it has a function of preventing substances that promote device deterioration such as moisture and oxygen from entering the device. Specific examples thereof include metals such as In, Sn, Pb, Au, Cu, Ag, Al, Ti, and Ni, MgO, SiO, and SiO.2 , Al2OThree, GeO, NiO, CaO, BaO, Fe2OThree, Y2OThreeTiO2Metal oxide such as MgF2, LiF, AlFThree, CaF2Metal fluorides such as polyethylene, polypropylene, polymethyl methacrylate, polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, tetrafluoro A copolymer obtained by copolymerizing a monomer mixture containing ethylene and at least one comonomer, a fluorinated copolymer having a cyclic structure in the copolymer main chain, a water-absorbing substance having a water absorption of 1% or more, a water absorption Examples include a moisture-proof substance of 0.1% or less.
There is no particular limitation on the method for forming the protective layer. For example, vacuum deposition, sputtering, reactive sputtering, MBE (molecular beam epitaxy), cluster ion beam, ion plating, plasma polymerization (high frequency excitation ions) Plating method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method, inkjet method can be applied.
[0060]
【Example】
EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto.
Example 1
A transparent support substrate was obtained by forming ITO with a thickness of 150 nm on a glass substrate of 25 mm × 25 mm × 0.7 mm (manufactured by Tokyo Sanyo Vacuum Co., Ltd.). After this transparent support substrate was etched and washed, copper phthalocyanine was evaporated to about 10 nm. Next, about 10 nm of TPD (N, N′-bis (3-methylphenyl) -N, N′-diphenylbenzidine) and about 60 nm of Alq (tris (8-hydroxyquinolinato) aluminum) as the third layer were sequentially added in order.-3~Ten-FourDeposition was performed in a Pa vacuum at a substrate temperature of room temperature. A patterned mask (a mask with a light emission area of 5mm x 5mm) is placed on the organic thin film, and magnesium: silver = 10: 1 is co-evaporated in 250nm in a vapor deposition system, and then 300nm of silver is deposited to produce element 101. did.
EL elements 102 to 112 having the same composition as 101 were prepared except that the TPD layer of the element 101 was changed to about 20 nm and an intermediate layer having the structure shown in Table 1 was newly provided between the TPD layer and the Alq layer. . Co-evaporation was performed at a mass ratio of host material: luminescent material = 10: 1 shown in Table 1, and the film thickness was 20 nm.
Using a source measure unit model 2400 manufactured by Toyo Technica Co., Ltd., a DC constant voltage is applied to the EL element to emit light, and the brightness is measured by Topcon's luminance meter BM-8. 11 was measured. The results are shown in Table 2.
[0061]
[Table 1]
[0062]
Embedded image
[0063]
[Table 2]
[0064]
Table 3 shows the results of the same luminance measurement and light emission surface observation after these elements were sealed in an autoclave substituted with argon gas and stored under heating conditions of 85 ° C. for 3 days.
[0065]
[Table 3]
[0066]
From the results shown in Table 2, the emission brightness of the orthometalated iridium complex was significantly increased in the element using the CBP, which is a known compound in the literature, and the compound of the present invention, compared to the element not using the orthomethylated iridium complex. It can be seen that the external quantum efficiency is also improved to 5% or more (7% or more compared to the 2% range). On the other hand, looking at the results after storage in Table 3, in the device using the compound of the present invention, the decrease in luminance was less than that of Comparative Samples 101 to 104, and the light emitting surface of the device was also good. It can be seen that the storage durability of the element is greatly improved.
[0067]
(Example 2)
On an ITO glass substrate etched and cleaned in the same manner as in Example 1, 40 mg of poly (N-vinylcarbazole (PVK)), 2,5-bis (1-naphthyl) -1,3,4-oxadiazole (DNPB) ) A solution of 12 mg and 10 mg of coumarin-6 dissolved in 3 ml of 1,2-dichloroethane was spin-coated. At this time, the film thickness of the organic layer was about 120 nm. Next, a cathode was deposited in the same manner as in Example 1 to produce an EL element 201.
EL elements 202 to 210 having the same composition as 201 were prepared except that the compound shown in Table 4 was added to element 201 instead of coumarin-6.
Using a source measure unit model 2400 manufactured by Toyo Technica Co., Ltd., a DC constant voltage is applied to the EL element to emit light, and the brightness is measured by Topcon's luminance meter BM-8. 11 was measured. The results are shown in Table 5.
[0068]
[Table 4]
[0069]
Embedded image
[0070]
[Table 5]
[0071]
As is apparent from the results in Table 5, in the same manner as in Example 1, the orthometalated iridium complex was used in the elements using CBP, which is a known compound in the literature, and the compound of the present invention. It can be seen that the emission luminance is considerably increased as compared with the non-complex, and the external quantum efficiency is improved to 3% or more as compared with less than 1%.
[0072]
【The invention's effect】
The organic electroluminescent element of the present invention is capable of emitting light with high brightness and high efficiency and is excellent in durability.

Claims (3)

  1. In a light-emitting element in which an organic light-emitting layer or an organic compound layer including an organic light-emitting layer is formed between a pair of electrodes provided on a substrate, the organic light-emitting layer has a condensed heterocyclic skeleton having a nitrogen atom in a condensed portion, Further, a compound represented by the following general formula (1) in which the aromatic heterocycle having at least one nitrogen atom at a position that is not a condensed part in the heteroaromatic ring is an imidazopyridine ring and the following general formula (7): An organic electroluminescent device comprising the above-described ortho-iridium complex .
    General formula (1)
    In the formula, X represents a carbon atom or a nitrogen atom. Z 1 and Z 2 each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.
    (Wherein, R 31, R 32 is .q 31, q 32 representing the substituent represents an integer of 0 to 4, when q 31 + q 32 is 1 or more .q 31, q 32 is 2 or more, A plurality of R 31 and R 32 may be the same or different from each other, n 3 represents an integer of 0 to 5, m 3 represents 1, 2, or 3. L 3 represents a ligand.)
  2. The organic electroluminescent element according to claim 1, wherein the compound represented by the general formula (1) is selected from the following compounds.
  3. The compounds represented by the general formula (1) HT-6, HT-7, HT-9, HT-12, an organic electroluminescent device of claim 2 wherein is selected from beauty HT-17.
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