JP4823730B2 - Luminescent layer compound and organic electroluminescent device - Google Patents

Luminescent layer compound and organic electroluminescent device Download PDF

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JP4823730B2
JP4823730B2 JP2006077013A JP2006077013A JP4823730B2 JP 4823730 B2 JP4823730 B2 JP 4823730B2 JP 2006077013 A JP2006077013 A JP 2006077013A JP 2006077013 A JP2006077013 A JP 2006077013A JP 4823730 B2 JP4823730 B2 JP 4823730B2
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正樹 古森
敏浩 山本
雄一 澤田
孝弘 甲斐
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新日鐵化学株式会社
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  The present invention relates to a novel light emitting layer compound and an organic electroluminescent device (hereinafter referred to as an organic EL device), and in particular, exhibits high brightness by using a phosphorescent dopant and a host compound having a specific structure in combination. The present invention relates to an organic EL element.

  In general, the organic EL element has a light emitting layer and a pair of counter electrodes sandwiching the layer as its simplest structure. That is, in an organic EL element, when an electric field is applied between both electrodes, electrons are injected from the cathode and holes are injected from the anode. These recombination energy levels in the light emitting layer change from the conduction band to the valence band. Utilizing the phenomenon of emitting light as energy when returning to.

  In recent years, EL devices using organic thin films have been developed. In particular, in order to improve luminous efficiency, the type of electrode is optimized for the purpose of improving the efficiency of carrier injection from the electrode, and consists of a hole transport layer made of aromatic diamine and 8-hydroxyquinoline aluminum complex (hereinafter referred to as Alq3). The development of a device with a light emitting layer as a thin film between the electrodes has greatly improved the light emission efficiency compared to conventional devices using single crystals such as anthracene. It has been promoted with the aim of putting it into practical use for high performance flat panels.

  In addition, as an attempt to increase the light emission efficiency of the device, the use of phosphorescence instead of fluorescence has been studied. Many devices, including those provided with the hole transport layer composed of the above aromatic diamine and the light emitting layer composed of Alq3, used fluorescence emission, but use phosphorescence emission, that is, triplet. If light emission from an excited state is used, an efficiency improvement of about three times is expected compared to a conventional device using fluorescence (singlet). For this purpose, it has been studied to use a coumarin derivative or a benzophenone derivative as a light emitting layer, but only an extremely low luminance was obtained. Thereafter, the use of a europium complex has been studied as an attempt to utilize the triplet state, but this also did not lead to highly efficient light emission. Many studies using phosphorescence have been conducted mainly on organometallic complexes such as iridium complexes as described in Patent Document 1 as phosphorescent dopants.

Special Table 2003-515897 JP 2001-313178 A JP 2002-352957 A Japanese Patent No. 3079909 JP 2005-104971 A JP 2005-213188

  On the other hand, a combination of a dopant material and a host material is important in order to obtain a practical light-emitting layer, and such a host material proposed is the carbazole compound introduced in Patent Document 2. CBP is mentioned. When CBP is used as the host material for the tris (2-phenylpyridine) iridium complex (hereinafter referred to as Ir (ppy) 3), a green phosphorescent light emitting material, CBP has a charge injection balance due to its ability to easily flow holes and electrons. Collapses, excess holes flow out to the electron transport side, and as a result, the light emission efficiency from Ir (ppy) 3 decreases.

  Further, 3-phenyl-4- (1′-naphthyl) -5-phenyl-1,2,4-triazole (hereinafter referred to as TAZ) disclosed in Patent Document 3 is also proposed as a host material for phosphorescent organic EL devices. However, the light emitting region is on the side of the hole transport layer because of the characteristic that electrons easily flow and holes do not easily flow. Therefore, depending on the material of the hole transport layer, the light emission efficiency from Ir (ppy) 3 may be lowered due to a compatibility problem with Ir (ppy) 3. For example, 4,4'-bis (N- (1-naphthyl) -N-phenylamino) biphenyl (hereinafter referred to as NPB), which is most often used as a hole transport layer in terms of high performance, high reliability, and long life Is not compatible with Ir (ppy) 3, and there is a problem in that energy transition occurs from Ir (ppy) 3 to NPB, resulting in a decrease in luminous efficiency.

  Furthermore, Patent Documents 4 to 6 disclose many fluorene compounds, but Patent Documents 4 and 6 only disclose a compound in which a carbazole group is directly bonded to the phenyl moiety of a bisphenylfluorene compound, via a linking group. Thus, it does not disclose the usefulness of a compound to which a carbazole group is bonded. By bonding a carbazole-substituted aromatic compound through a linking group, a host material having high triplet energy is obtained. Further, Patent Document 5 discloses a compound in which two carbazole groups are substituted with a fluorene compound directly or via a linking group, but does not indicate the usefulness of a compound in which three or more carbazole groups are substituted. . By substituting three or more carbazole groups, thermal stability is improved, and high driving stability can be expected with high efficiency.

  In order to apply the organic EL element to a display element such as a flat panel display, it is necessary to improve the light emission efficiency of the element and at the same time to ensure sufficient stability during driving. An object of this invention is to provide the practically useful organic EL element which has high efficiency and high drive stability in view of the said present condition, and a compound suitable for it.

  As a result of intensive studies, the present inventors have found that the above-mentioned problems can be solved by using a bisphenylfluorene compound having a specific structure as a light-emitting layer compound of an organic EL device, and the present invention has been completed. It was.

The present invention is a light emitting layer compound represented by the following general formula (1).
(In the formula, Ar 1 represents a divalent linking group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 4 to 18 carbon atoms or an aromatic heterocyclic group which is not a condensed ring structure, and X is an oxygen atom or a sulfur atom. , A carbonyl group, a carbonyloxy group, an amide group or a sulfonyl group which may have a substituent, wherein R is hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted carbon group having 4 to 6 carbon atoms which is not a condensed ring structure. 18 represents an aromatic hydrocarbon group or an aromatic heterocyclic group, and a plurality of Ar 1 or R may be the same or different. M and n represent an integer of 1 or 2.)

Moreover, this invention is a light emitting layer compound represented by following General formula (2).
(In the formula, Ar 1 represents a divalent linking group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 4 to 18 carbon atoms or an aromatic heterocyclic group that is not a condensed ring structure, X represents a direct bond, R represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 4 to 18 carbon atoms or an aromatic heterocyclic group that is not a condensed ring structure, and a plurality of Ar 1 or R are the same Or m and n represent an integer of 1 or 2, and m + n is 3 or 4.)

Moreover, this invention is a light emitting layer compound represented by following General formula (3).
(In the formula, Ar 1 , X and R are the same as those in the general formula (1). M and n represent an integer of 1 or 2, and m + n is 3 or 4.)

Moreover, this invention is a light emitting layer compound represented by following General formula (4).
(In the formula, R is the same as in the general formula (1). X represents an oxygen or sulfur atom.)

  Furthermore, the present invention provides an organic electroluminescent device having a light emitting layer between an anode and a cathode laminated on a substrate, wherein the light emitting layer comprises a phosphorescent dopant and any one of the above light emitting layer compounds as a host material. It is an organic electroluminescent element characterized by containing as.

  The present invention is also the above-described organic electroluminescent device comprising a hole injecting and transporting layer between the anode and the light emitting layer and an electron injecting and transporting layer between the cathode and the light emitting layer. Furthermore, the present invention is the above organic electroluminescent device comprising a hole blocking layer between the light emitting layer and the electron injecting and transporting layer.

The light emitting layer compound of the present invention is any one of the compounds represented by the general formulas (1) to (4). Two or more light emitting layer compounds of the present invention can be used in combination.
The compounds represented by the general formulas (1), (3) and (4) are carbazole-substituted aromatics via a divalent linking group such as an oxygen atom, a sulfur atom or a carbonyl group at the phenyl moiety of the bisphenylfluorene compound. By bonding a compound, it is possible to provide a practically useful organic EL device having a high triplet energy and high efficiency and high driving stability by reducing the conjugation property of the molecular skeleton. In addition, the compounds represented by the general formulas (2) and (3) can achieve higher stability by bonding three or more carbazole substituents.

In the general formulas (1) to (3), Ar 1 is preferably the following group.
A divalent aromatic hydrocarbon group or aromatic heterocyclic group generated from a benzene ring, biphenyl ring, terphenyl ring, furan ring, thiophene ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, etc. They have only a single ring structure and are common in that they do not expand the conjugated system with the carbazole ring.

In the general formulas (1) and (3), X is preferably the following group.
Common in that it is an oxygen atom, sulfur atom, carbonyl group, carbonyloxy group, N-phenylamide group or sulfonyl group, and has a structure capable of cutting the conjugated system of the phenyl group of the biphenylfluorene compound and the carbazole-substituted aromatic To do.

In the general formulas (1) to (4), R is preferably the following group.
C1-C4 alkyl groups such as methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, tert-butyl, benzene ring, biphenyl ring, terphenyl ring, furan ring, thiophene ring, pyridine ring , A monovalent group formed from a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, etc., which are common in that they are resistant to electrical redox and have excellent thermal stability.

In the general formulas (1) to (4), when there are a plurality of X, Ar 1 and R, these may be the same or different. However, in synthesizing these compounds, X, Ar 1 and R at corresponding positions are advantageously the same group.

  As one method for synthesizing the compound represented by the general formula (1), the corresponding fluorene derivative and the corresponding halogenated phenylcarbazole are used in an organic solvent or without a solvent in the presence of a base and a catalyst in a nitrogen atmosphere. It can be obtained by reacting at a temperature of about 100 to 200 ° C. for about 1 to 90 hours. Examples of the halogen atom of the halogenated phenylcarbazole include chlorine, bromine and iodine. The bases used are inorganic bases such as potassium carbonate, sodium carbonate, cesium carbonate, potassium phosphate, lithium hydroxide, sodium hydroxide, sodium tert-butoxide, potassium tert-butoxide, pyridine, picoline, triethylamine and the like. Organic bases. Catalysts include copper powders, copper oxides, copper halides, copper sulfates and other copper catalysts, or palladium sources such as palladium acetate and bis (dibenzylideneacetone) palladium and ligands such as tri-tert-butylphosphine. The palladium complex catalyst formed is mentioned. The solvent should just be a thing which can melt | dissolve a raw material and can make it react. Examples thereof include solvents such as toluene, xylene, dioxane, tetralin, quinoline, nitrobenzene, dimethyl sulfoxide, N, N-dimethylformamide and the like.

  After completion of the reaction, water is added to separate the organic layer, which is concentrated, washed with a low boiling point solvent such as ethyl acetate, and dried under reduced pressure to obtain the compound of the present invention. In order to enhance the performance of the compound of the present invention as a light emitting layer compound of an organic EL material, particularly as a host material, it is preferable to further sublimate and purify it.

  Next, although the preferable specific example of a compound represented by General formula (1)-(4) is shown below, it is not limited to these. In addition, the number described under the chemical formula is a compound number.

  The phosphorescent dopant material in the light emitting layer preferably contains an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold. Such organometallic complexes are known in the above-mentioned patent documents and the like, and these can be selected and used.

  Preferable phosphorescent dopants include complexes such as Ir (ppy) 3 having a noble metal element such as Ir as a central metal, complexes such as Ir (bt) 2 · acac3, and complexes such as PtOEt3. Specific examples of these complexes are shown below, but are not limited to the following compounds.

  The amount of the phosphorescent dopant contained in the light emitting layer is preferably in the range of 5 to 10% by weight.

  Next, an organic EL device using the light emitting layer compound of the present invention will be described.

The organic EL device of the present invention is an organic EL device having at least one light-emitting layer between an anode and a cathode laminated on a substrate, and the light-emitting layer includes a phosphorescent dopant, and general formulas (1) to (1) to (1). It contains the compound represented by (4).
As a preferable structure of the organic EL element, a structure having a hole injecting and transporting layer between the anode and the light emitting layer and an electron injecting and transporting layer between the cathode and the light emitting layer, or between the light emitting layer and the electron injecting and transporting layer. There is a structure having a hole blocking layer.

  Next, the structure of the organic EL element of the present invention will be described with reference to the drawings. However, the structure of the organic EL element of the present invention is not limited to the illustrated one.

  FIG. 1 is a cross-sectional view schematically showing a structural example of a general organic EL element used in the present invention, wherein 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, Represents a light emitting layer, 6 represents an electron transport layer, and 7 represents a cathode. The organic EL device of the present invention has a substrate, an anode, a light emitting layer, and a cathode as essential layers. In addition to the layers other than the essential layers, the organic EL device preferably has a hole injecting and transporting layer and an electron injecting and transporting layer. A hole blocking layer is preferably provided between the light emitting layer and the electron injecting and transporting layer. The hole injection / transport layer means either or both of a hole injection layer and a hole transport layer, and the electron injection / transport layer means either or both of an electron injection layer and an electron transport layer.

  In addition, it is also possible to laminate | stack the cathode 7, the electron carrying layer 6, the light emitting layer 5, the positive hole transport layer 4, and the anode 2 in this order on the board | substrate 1 in the reverse structure, FIG. It is also possible to provide the organic EL device of the present invention between two substrates, at least one of which is highly transparent. Also in this case, layers can be added or omitted as necessary.

  The present invention can be applied to any of an organic EL element having a single element, an element having a structure arranged in an array, and a structure having an anode and a cathode arranged in an XY matrix. According to the organic EL device of the present invention, the light emitting layer contains a compound having a specific skeleton and a phosphorescent light emitting dopant, so that the light emitting efficiency is higher than that of a conventional device using light emission from a singlet state and driving. A device with greatly improved stability can be obtained, and excellent performance can be exhibited in application to full-color or multi-color panels.

  Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is of course not limited to these examples, and can be implemented in various forms as long as the gist thereof is not exceeded. is there.

Example 1
Synthesis of Compound 1 9- (bis (p-hydroxyphenyl)) fluorene (BPFL) 5.43 g (15.40 mmol), p-iodophenylcarbazole 15.00 g (40.43 mmol), copper iodide in a 500 ml three-necked flask purged with nitrogen 2.98 g (15.65 mmol), N, N′-dimethylglycine hydrochloride 3.00 g (21.49 mmol) and 16.40 g (50.33 mmol) of cesium carbonate were added, and 300 ml of 1,4-dioxane was added and stirred. . Thereafter, the mixture was heated to 120 ° C. and stirred for 72 hours. After cooling to room temperature, the reaction solution was filtered and the solvent was distilled off under reduced pressure. The obtained brown powder (19 g) was treated with activated carbon and purified by silica gel chromatography to obtain a white solid (14.36 g, yield 89.2%).
Compound 1 had an FD-MS (M +) of 832 and a melting point of 169 ° C.

Example 2
Synthesis of Compound 14 Under a nitrogen atmosphere, 17 g (0.39 mol) of sodium hydride (55%) was allowed to act on 71 g (0.43 mol) of carbazole in anhydrous N, N′-dimethylformamide in a 200 ml three-necked flask. Bromo-3,5-difluorobenzene (25 g, 0.13 mol) was added, and the mixture was stirred at 80 ° C. for 10 hours, 120 ° C. for 0.5 hour, and 140 ° C. for 1 hour. 1000 ml of water and 300 ml of methanol were added to the resulting solution and filtered. The obtained solid was washed 3 times with 500 ml of water and 3 times with 500 ml of methanol. Thereafter, crystallization was performed with THF and methanol to obtain 32 g (yield 58.3%) of 1-bromo-3,5-bis (N-carbazolyl) benzene.

  In a nitrogen atmosphere, charge 1000 ml of anhydrous THF and 1.46 g (60 mmol) of magnesium into a 1000 ml three-necked flask, and slowly add a solution of 24.3 g (50.0 mmol) of 1-bromo-3,5-bis (N-carbazolyl) benzene in 220 ml of THF under reflux of THF. And dripped. After 2 hours, the mixture was cooled to room temperature, and the resulting solution was added dropwise to a THF 150 ml solution of trimethoxyborane 6.23 g (60.0 mmol) at 0 ° C. and stirred for 1 hour. Then, methanol and hydrochloric acid were added and stirred for 12 hours. The resulting solution was filtered off and washed with ethyl acetate and water. The organic layer and the aqueous layer were separated and dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained solid was purified by silica gel chromatography to obtain 14.6 g (yield 64.5%) of 3,5-biscarbazolylphenylboronic acid.

In a 500 ml three-necked flask, 10.7 g (15 mmol) of 9- (bis (p-iodophenyl)) fluorene, 13.9 g (32.5 mmol) of 3,5-biscarbazolylphenylboronic acid, 1.73 g (1.5 mmol) of tetrakistriphenylphosphine palladium ), 30 ml of 2M sodium carbonate aqueous solution was added, and 150 ml of toluene was added thereto and stirred. Thereafter, the mixture was heated to 90 ° C. and stirred for 3.5 hours. After cooling to room temperature, the reaction solution was filtered and the solvent was distilled off under reduced pressure. After treating 30.5 g of the obtained brown powder with activated carbon, silica gel chromatography was performed, and the obtained solid was crystallized using toluene-hexane to obtain a white solid 9.9 g (yield 58.4%). .
Compound 14 had an FD-MS (M +) of 1130 and a melting point of 381 ° C.

Example 3
Compound 1 and Ir (ppy) 3 were vapor-deposited from different vapor deposition sources on a glass substrate under vacuum conditions of 4.0 × 10 -4 Pa and the concentration of Ir (ppy) 3 was 7.0%. A thin film having a thickness of 50 nm was formed at 1.0 cm / sec.
The prepared thin film was evaluated with a fluorescence measuring apparatus. The excitation wavelength is the maximum absorption wavelength of Compound 1, and the light emitted at that time was observed. The results are shown in Table 1.

Example 4
A thin film was prepared in the same manner as in Example 3 except that compound 14 was used as the host material, and the prepared thin film was evaluated with a fluorescence measuring apparatus. The excitation wavelength is the maximum absorption wavelength of Compound 14, and the light emitted at that time was observed. The results are shown in Table 1.

Comparative Example 1
The same procedure as in Examples 3 and 4 was performed, except that the thin film main component was changed to Alq3 to prepare a thin film. The results are shown in Table 1.

  When compound 1 or compound 14 is used as the main material of the light emitting layer, energy transitions to Ir (ppy) 3 and light emission from Ir (ppy) 3 is observed, but when Alq3 is used, Ir It can be seen that energy does not transition to (ppy) 3, and Alq3 itself emits fluorescence.

Example 5
In FIG. 1, an organic EL element having a configuration in which the hole injection layer is omitted and an electron injection layer is added is prepared. Each thin film was laminated at a vacuum degree of 4.0 × 10 −4 Pa by a vacuum deposition method on a glass substrate on which an anode made of ITO having a thickness of 150 nm was formed. First, NPB was formed to a thickness of 60 nm on ITO as a hole transport layer.
Next, Compound 1 and Ir (ppy) 3 were co-deposited from different vapor deposition sources on the hole transport layer as a light emitting layer to form a thickness of 25 nm. At this time, the concentration of Ir (ppy) 3 was 7.0%. Next, Alq3 was formed to a thickness of 50 nm as an electron transport layer. Further, lithium fluoride (LiF) was formed to a thickness of 0.5 nm as an electron injection layer on the electron transport layer. Finally, on the electron injection layer, aluminum (Al) was formed as an electrode to a thickness of 170 nm, and an organic EL element was produced.

Example 6
An organic EL device was produced in the same manner as in Example 5 except that Compound 14 was used as the light emitting layer.

When an external power source was connected to the obtained organic EL element and a DC voltage was applied, it was confirmed that the organic EL element had the light emission characteristics as shown in Table 2. In Table 2, the luminance, voltage, and luminous efficiency show values at 10 mA / cm 2 . The maximum wavelength of the device emission spectrum was 517 nm, indicating that light emission from Ir (ppy) 3 was obtained.

Comparative Example 2
An organic EL device was prepared in the same manner as in Example 5 except that HMTPD was used as the hole transport layer and TAZ was used as the main component of the light emitting layer.

Comparative Example 3
An organic EL device was produced in the same manner as in Example 5 except that TAZ was used as the main component of the light emitting layer.

Comparative Example 4
In Comparative Example 3, an organic EL device was produced in the same manner as in Example 5 except that the following compound described in Japanese Patent No. 3079909 was used instead of TAZ as the host material of the light emitting layer.

  The organic EL device of the present invention can emit light with high luminance and high efficiency at a low voltage. Accordingly, the organic EL device according to the present invention is a flat panel display (for example, for OA computers or wall-mounted televisions), an in-vehicle display device, a light source utilizing characteristics of a mobile phone display or a surface light emitter (for example, a light source of a copying machine, a liquid crystal). It can be applied to backlight sources for displays and instruments, display panels, and indicator lights, and its technical value is great.

The schematic cross section which showed an example of the organic EL element.

Explanation of symbols

  1 substrate, 2 anode, 3 hole injection layer, 4 hole transport layer, 5 light emitting layer, 6 electron transport layer, 7 cathode

Claims (7)

  1. A light emitting layer compound represented by the following general formula (1).
    (In the formula, Ar 1 represents a divalent group consisting of a substituted or unsubstituted C 4-18 aromatic hydrocarbon group or aromatic heterocyclic group that is not a condensed ring structure, and X is an oxygen atom, a sulfur atom, Represents a carbonyl group, a carbonyloxy group, an amide group or a sulfonyl group which may have a substituent, and R represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted carbon atom having 4 to 18 carbon atoms which is not a condensed ring structure. And a plurality of Ar 1 or R may be the same or different. M and n represent an integer of 1 or 2.)
  2. The light emitting layer compound shown by following General formula (2).
    (In the formula, Ar 1 represents a divalent group consisting of a substituted or unsubstituted C 4-18 aromatic hydrocarbon group or aromatic heterocyclic group that is not a condensed ring structure, X represents a direct bond, and R Represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group or aromatic heterocyclic group having 4 to 18 carbon atoms which is not a condensed ring structure, and a plurality of Ar 1 or R are the same And m and n are integers of 1 or 2, but m + n is 3 or 4.)
  3. The light emitting layer compound of Claim 1 shown by following General formula (3).
    (In the formula, m and n represent an integer of 1 or 2, but m + n is 3 or 4. Ar 1 , X and R are the same as those in the general formula (1).)
  4. The light emitting layer compound of Claim 1 shown by following General formula (4).
    (In the formula, X represents an oxygen or sulfur atom, and R is the same as the general formula (1).)
  5.   It is an organic electroluminescent element which has a light emitting layer between the anode and cathode which were laminated | stacked on the board | substrate, Comprising: This light emitting layer is a phosphorescent dopant and the light emitting layer compound in any one of Claims 1-4. An organic electroluminescent element characterized by containing as a host material.
  6.   The organic electroluminescent device according to claim 5, further comprising a hole injecting and transporting layer between the anode and the light emitting layer and an electron injecting and transporting layer between the cathode and the light emitting layer.
  7.   The organic electroluminescence device according to claim 5 or 6, further comprising a hole blocking layer between the light emitting layer and the electron injecting and transporting layer.
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