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Timestamp: 2014-07-13 01:54:22
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Matched Legal Cases: ['Application No. 2001', 'Application No. 7', 'Application No. 8', 'Application No. 10', 'Application No. 10', 'Application No. 10', 'Application No. 9']

Patent US6805977 - Condensed eight-ring aromatic compound, and organic EL element and organic ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign in<nobr>Advanced Patent Search</nobr>PatentsThe object of the present invention is to provide an organic EL element which utilizes a novel condensed eight-ring aromatic compound, and has high color purity of red light and excellent light-emitting efficiency, light-emitting luminance and the like. The organic EL element of the present invention...http://www.google.com/patents/US6805977?utm_source=gb-gplus-sharePatent US6805977 - Condensed eight-ring aromatic compound, and organic EL element and organic EL display using the sameAdvanced Patent SearchPublication numberUS6805977 B2Publication typeGrantApplication numberUS 10/104,013Publication dateOct 19, 2004Filing dateMar 25, 2002Priority dateAug 29, 2001Fee statusPaidAlso published asCN1239446C, CN1403427A, DE60220225D1, DE60220225T2, EP1289343A1, EP1289343B1, US20030082404Publication number10104013, 104013, US 6805977 B2, US 6805977B2, US-B2-6805977, US6805977 B2, US6805977B2InventorsWataru Sotoyama, Hiroyuki Sato, Azuma Matsuura, Toshiaki NarusawaOriginal AssigneeFujitsu LimitedExport CitationBiBTeX, EndNote, RefManPatent Citations (15), Non-Patent Citations (35), Referenced by (18), Classifications (28), Legal Events (8) External Links: USPTO, USPTO Assignment, EspacenetCondensed eight-ring aromatic compound, and organic EL element and organic EL display using the sameUS 6805977 B2Abstract The object of the present invention is to provide an organic EL element which utilizes a novel condensed eight-ring aromatic compound, and has high color purity of red light and excellent light-emitting efficiency, light-emitting luminance and the like. The organic EL element of the present invention has, in between a positive electrode and a negative electrode, an organic thin-film layer including a light-emitting layer. The organic thin-film layer contains the condensed eight-ring aromatic compound which has a number of regions where substituents can be introduced is any of 14, 16 and 18, and the condensed eight-ring aromatic compound has a point-symmetrical skeleton.
CROSS-REFERENCE TO RELATED APPLICATIONS This application is based upon and claims priority of Japanese Patent Applications No. 2001-259684, filed in Aug. 29, 2001, and Japanese Patent Application No. 2001-361504, filed in Nov. 27, 2001, the contents being incorporated herein by reference.
For example, an organic EL element using a DCM dye is disclosed as an organic EL element which can emit red (R) light in C. W. Tang, S. A. VanSlyke, and C. H. Chen, �Journal of Applied Physics�, Vol. 65, 3610 (1989). Further, organic EL elements, which use a porphin compound or a porphine compound which can emit red light, have been proposed in Japanese Patent Application Laid-Open (JP-A) No. 9-13024 (Japanese Patent Application No. 7-160676), JP-A No. 9-296166 (Japanese Patent Application No. 8-111437), JP-A No. 11-251061 (Japanese Patent Application No. 10-50464), JP-A No. 11-251062 (Japanese Patent Application No. 10-50465), a Japanese National Re-Publication (International Publication No. WO98/00474, Japanese Patent Application No. 10-503982), and the like. Moreover, an organic EL element using a bisanthrene compound which can emit red light has been disclosed in JP-A No. 11-144868 (Japanese Patent Application No. 9-303047).
SUMMARY OF THE INVENTION The present invention focuses on addressing these concerns, overcoming the aforementioned drawbacks of the prior art, and achieving the following object. Namely, an object of the present invention is to provide a condensed eight-ring aromatic compound which has high color purity of red light and excellent light-emitting efficiency, light-emitting luminance and the like and which is suitable for an organic EL element, an organic EL element which uses the condensed eight-ring aromatic compound and has high color purity of red light and excellent light-emitting efficiency, light-emitting luminance and the like, and an organic EL display which is high-performance and utilizes the organic EL element.
BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a schematic explanatory view for explaining an example of a layer structure in an organic EL element of the present invention.
DESCRIPTION OF THE PREFERRED EMBODIMENTS <Condensed Eight-Ring Aromatic Compound>
Examples of the condensed eight-ring aromatic compound are condensed eight-ring aromatic hydrocarbon compounds and derivatives thereof. Specifically, compounds expressed by any of following structural formulas (1) through (3) can be suitably used. Note that the condensed eight-ring aromatic compound expressed by structural formula (1) is a dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene compound (hereinafter simply called �dinaphthopyrene compound�), the condensed eight-ring aromatic compound expressed by structural formula (2) is a 2,3,8,9-dibenzanthanthrene compound (hereinafter simply called �dibenzanthanthrene compound�), and the condensed eight-ring aromatic compound expressed by structural formula (3) is a peri-naphthacenonaphthacene compound (hereinafter simply called �naphthacenonaphthacene compound�). In structural formula (1), R1 through R18 may be the same or may be different to each other, and represent hydrogen atoms or substituents (but cases in which all are hydrogen atoms are excluded). In structural formula (2), R1 through R16 may be the same or may be different to each other, and represent hydrogen atoms or substituents (but cases in which all are hydrogen atoms are excluded). In structural formula (3), R1 through R14 may be the same or may be different to each other, and represent hydrogen atoms or substituents (but cases in which all are hydrogen atoms are excluded).
The alkoxy group is expressed by �OR (where R represents the aforementioned alkyl groups). Examples include methoxy, ethoxy, propoxy, isopropoxy, cyclopropoxy, butoxy, isobutoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, and the like.
When, in structural formula (1), R1 through R8 and R10 through R17 are hydrogen atoms and R9 and R18 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., in the case of �structure 1�), the compound is stable. Therefore, the condensed eight-ring aromatic compound (the dinaphthopyrene compound) can be suitably used in the organic EL element. R9 and R18 being the same is preferable from the standpoint that the effects are marked.
Similarly to above, in structural formula (1), a case in which R2 through R9 and R11 through R18 are hydrogen atoms and R1 and R10 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., the case of �structure 2�), a case in which R1 through R7, R9 through R16, and R18 are hydrogen atoms and R8 and R17 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., the case of �structure 3�), a case in which R1 through R6, R8 through R15, and R17 through R18 are hydrogen atoms and R7 and R16 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., the case of �structure 4�), and the like are also preferable.
When, in structural formula (2), R1 through R6, R8 through R14,and R16 are hydrogen atoms and R7 and R15 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., in the case of �structure 1�), the compound is stable. Therefore, the condensed eight-ring aromatic compound (the dibenzanthanthrene compound) can be suitably used in the organic EL element. R7 and R15 being the same is preferable from the standpoint that the effects are marked.
Similarly to above, in structural formula (2), a case in which R1 through R5, R7 through R13, and R15 through R16 are hydrogen atoms and R6 and R14 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., the case of �structure 2�), a case in which R1 through R7 and R9 through R15 are hydrogen atoms and R8 and R16 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., the case of �structure 3�), a case in which R2 through R8 and R10 through R16 are hydrogen atoms and R1 and R9 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., the case of �structure 4�), and the like are also preferable.
When, in structural formula (3), R1 through R5, R7 through R12,and R14 are hydrogen atoms and R6 and R13 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., in the case of �structure 1�), the compound is stable. Therefore, the condensed eight-ring aromatic compound (naphthacenonaphthacene) can be suitably used in the organic EL element. R6 and R13 being the same is preferable from the standpoint that the effects are marked.
Similarly to above, in structural formula (3), a case in which R1 through R4, R6 through R11, and R13 through R14 are hydrogen atoms and R5 and R12 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., the case of �structure 2�), a case in which R1 through R6 and R8 through R13 are hydrogen atoms and R7 and R14 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., the case of �structure 3�), a case in which R2 through R7 and R9 through R14 are hydrogen atoms and R1 and R8 are selected from phenyl groups, phenylamino groups, and diphenylamino groups (i.e., the case of �structure 4�), and the like are also preferable.
The host compound is preferably a compound whose light-emitting wavelength is in the vicinity of the light absorption wavelength of the condensed eight-ring aromatic compound. Among these, because the light absorption wavelength of the condensed eight-ring aromatic compound is 500 to 650 nm, compounds, whose light absorption wavelength is at the shorter wavelength side of the condensed eight-ring aromatic compound and whose light-emitting wavelength is in a vicinity of the light absorption wavelength of the condensed eight-ring aromatic compound, are preferable. Specifically, the aluminum quinoline complex (Alq) (main light-emitting wavelength=530 nm) expressed by the following structural formula, 9,9′-bianthryl (main light-emitting wavelength=460 nm) expressed by the following structural formula, 4,4′-bis(9-carbazolyl)-biphenyl (CBP) (main light-emitting wavelength=380 nm) expressed by the following structural formula, 4,4′-bis(2,2′-diphenylvinyl)-1,1′-biphenyl (DPVBi) (main light-emitting wavelength=470 nm) expressed by the following structural formula, p-sexiphenyl (main light-emitting wavelength=400 nm) expressed by the following structural formula, 1,3,6,8-tetraphenylpyrene (main light-emitting wavelength=440 nm) expressed by the following structural formula, N,N′-dinaphthyl-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (NPD) (main light-emitting wavelength=430 nm) expressed by the following structural formula, and the like are preferable. The Aluminum quinoline complex (Alq) is particularly preferable. The host compound, such as the aluminum quinoline complex (Alq) or the like, may have a substituent which is appropriately selected within a range in which the overlapping of the light-emitting wavelength of the host compound on the absorption wavelength of the condensed eight-ring aromatic compound is not eliminated. For example, in the case of the aluminum quinoline complex (Alq), the methyl substituents expressed by the following structural formulas, or the like can suitably be used. When the light-emitting layer contains the host compound, a material having an excellent film forming ability can be selected as the host compound. Thus, there is the advantage that the light-emitting layer can have an excellent film forming ability regardless of the film forming ability of the condensed eight-ring aromatic compound itself. Further, in the light-emitting layer, when the recombination site, at which the positive holes injected from the positive electrode and the electrons injected from the negative electrode recombine, is the host compound, first, the host compound is excited. Then, in cases in which the light-emitting wavelength of the host compound and the absorption wavelength of the guest compound (the condensed eight-ring aromatic compound) overlap, the excitation energy effectively moves from the host compound to the guest compound (the condensed eight-ring aromatic compound). The host compound returns to the ground state without emitting light, and only the guest compound (the condensed eight-ring aromatic compound) which has moved to an excited state releases the excitation energy as red light. Thus, this is advantageous in that emission of red light of a high color purity is obtained, and the light-emitting efficiency, light-emitting luminance and the like are excellent. Generally when the light emitting molecules exist alone or in high density in the thin layer, generates an interaction between the light emitting molecules referred to as �concentration quenching� which is a light emission efficiency deterioration phenomenon caused by the molecules coming in closer contact with each other. However, in the aforementioned light-emitting layer, the condensed eight-ring aromatic compound is dispersed at a relatively low concentration in the host compound, the aforementioned �concentration quenching� is effectively suppressed, and the light-emitting efficiency is excellent.
When the light-emitting layer contains n types of host compounds, materials having an excellent film forming ability can be selected as the first host compound through the nth host compound. Thus, there is the advantage that the light-emitting layer can have an excellent film forming ability regardless of the film forming ability of the condensed eight-ring aromatic compound itself. Further, in the light-emitting layer, when the recombination site, at which the positive holes injected from the positive electrode and the electrons injected from the negative electrode recombine, is the kth host compound, first, the kth host compound is excited. Then, in a case in which the light-emitting wavelength of the kth host compound and the absorption wavelength of the (k+1)th host compound overlap, and the light-emitting wavelength of the (k+1)th host compound and the absorption wavelength of the (k+2)th host compound overlap, . . . , and the light-emitting wavelength of the nth host compound and the absorption wavelength of the guest compound (the condensed eight-ring aromatic compound) overlap, the excitation energy effectively moves from the host compounds to the guest compound (the condensed eight-ring aromatic compound). The host compounds return to the ground state without emitting light, and only the guest compound (the condensed eight-ring aromatic compound) which has moved to an excited state releases the excitation energy as red light. Thus, this is advantageous in that emission of red light of a high color purity is obtained, and the light-emitting efficiency, light-emitting luminance and the like are excellent. Further, at the light-emitting layer, the condensed eight-ring aromatic compound is dispersed at a relatively low concentration in the first host compound through the nth host compound, the aforementioned �concentration quenching� is effectively suppressed, and the light-emitting efficiency is excellent.
�Positive Electrode�
�Negative Electrode�
�Positive Hole Injecting Layer�
�Positive Hole Transporting Layer�
�Electron Transporting Layer�
Among these layer structures, when (4) positive electrode/positive hole transporting layer/light-emitting layer/electron transporting layer/negative electrode is illustrated, it is as in FIG. 1. An organic EL element 10 has a layer structure in which a positive electrode 14 (e.g., an ITO electrode) formed on a glass substrate 12, a positive hole transporting layer 16, a light-emitting layer 18, an electron transporting layer 20, and a negative electrode 22 (e.g., an Al�Li electrode) are layered in that order. The positive electrode 14 (e.g., an ITO electrode) and the negative electrode 22 (e.g., an Al�Li electrode) are connected to each other via a power source. An organic thin-film layer 24 for emitting red light is formed by the positive hole transporting layer 16, the light-emitting layer 18, and the electron transporting layer 20.
As methods for making the organic EL display a full-color type display, for example, as disclosed in �Gekkan Display�, September 2000, pp. 33-37, there are a three-color light-emitting method in which organic EL elements, which emit lights corresponding to the three primary colors (blue (B), green (G), red (R)), respectively, are disposed on a substrate; a white color method in which white light emitted by an organic EL element for emitting white light is passed through a color filter so as to be divided into the three primary colors; a color conversion method in which blue light emitted by an organic EL element for emitting blue light is passed through a fluorescent dye layer and converted into red (R) and green (G); and the like. However, because the organic EL element of the present invention which is used is for emitting red light, the present invention can particularly suitably utilize the three-color light-emitting method.
The organic EL element for emitting green light is not particularly limited, and can be appropriately selected from among known elements. For example, an element whose layer structure is ITO (positive electrode)/NPD/Alq/Al�Li (negative electrode), or the like is suitable.
The organic EL element for emitting blue light is not particularly limited, and can be appropriately selected from among known elements. For example, an element whose layer structure is ITO (positive electrode)/NPD/DPVBi expressed by the following formula/Alq/Al�Li (negative electrode), or the like is suitable. DPVBi is 4,4′-bis(2,2′-diphenyl-ethane-1-yl)-biphenyl. The mode of the organic EL display is not particularly limited, and can be appropriately selected in accordance with the object. Suitable examples include a passive matrix panel, an active matrix panel, and the like, such as those disclosed in �Nikkei Electronics�, No. 765, Mar. 13, 2000, pp. 55-62.
EXAMPLES Hereinafter, Examples of the present invention will be concretely described. However, the present invention is not to be limited in any way to these Examples.
Synthesis Example 1 Synthesis of dinaphtho(2′:3′-3:4) (2″:3″-8:9)pyrene
Dinaphtho (2′:3′-3:4) (2″:3″-8:9)pyrene represented by the following formula is synthesized in accordance with a publication (�Journal of the Chemical Society�, 1949, p. 2013). Synthesis Example 2 Synthesis of 5,10-diphenyl-dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene
Dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene is dissolved in carbon tetrachloride. While the resultant mixture is being cooled, 1 mol equivalent of bromine is added thereto. The mixture is reacted for 4 hours and brominated. Thereafter, the mixture is purified in accordance with a usual method, and 5,10-dibromodinaphtho(2′:3′-3:4) (2″:3″-8:9)pyrene is obtained. 2 mol equivalent of phenylboronic acid [Ph�B(OH)2] (where �Ph� represents a phenyl group) is refluxed and reacted for two hours with the 5,10-dibromodinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene obtained in this way, in a xylene/2M sodium carbonate aqueous solution, by using 0.01 mol equivalent of tetraquis(triphenylphosphine)palladium (0) [Pd(PPh3)4] (where �Ph� represents a phenyl group) as a catalyst. Thereafter, the resultant mixture is purified in accordance with a usual method, and the 5,10-diphenyl-dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene expressed by the following formula is synthesized. (Note that, in the formula, �Ph� represents a phenyl group.) Synthesis Example 3 Synthesis of 5,10-bis(phenylamino)dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene
Dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene is dissolved in carbon tetrachloride. While the resultant mixture is being cooled, 1 mol equivalent of bromine is added thereto. The mixture is reacted for 4 hours and brominated. Thereafter, the mixture is purified in accordance with a usual method, and 5,10-dibromodinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene is obtained. Phenylamine, potassium carbonate, and copper powder are added to the 5,10-dibromodinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene obtained in this way, and the mixture is reacted for 30 hours at 200� C. After the reaction solution is diluted with water, the reactant is eluted with chloroform. Thereafter, the resultant substance is purified in accordance with a usual method, and the 5,10-bis(phenylamino)dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene represented by the following formula is synthesized. (Note that, in the formula, �Ph� represents a phenyl group.) Synthesis Example 4 Synthesis of 5,10-bis(diphenylamino)dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene
Dinaphthopyrene is dissolved in carbon tetrachloride. While the resultant mixture is being cooled, 1 mol equivalent of bromine is added thereto. The mixture is reacted for 4 hours and brominated. Thereafter, the mixture is purified in accordance with a usual method, and 5,10-dibromodinaphthopyrene is obtained. Diphenylamine, potassium carbonate, and copper powder are added to the 5,10-dibromodinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene obtained in this way, and the mixture is reacted for 30 hours at 200� C. After the reaction solution is diluted with water, the reactant is eluted with chloroform. Thereafter, the resultant substance is purified in accordance with a usual method, and the 5,10-bis(diphenylamino)dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene represented by the following formula is synthesized. (Note that, in the formula, �Ph� represents a phenyl group.) Example 1 A laminated-type organic EL element using dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene in the light-emitting layer is prepared as follows. Namely, a glass substrate, on which ITO electrodes are formed as positive electrodes, is washed with water, acetone and isopropyl alcohol. Using a vacuum vapor deposition device (degree of vacuum=1�10−6 Torr (1.3�10−4 Pa), substrate temperature=room temperature), TPD serving as a positive hole transporting layer is covered on the ITO electrodes so as to be a thickness of 50 nm. Next, a light-emitting layer having a thickness of 20 nm is formed simultaneously by vapor depositing, on the positive hole transporting layer formed by the TPD, dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene and Alq such that the Alq is 99 molecules (99 mol) to 1 molecule (1 mol) of the dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene. Then, Alq serving as an electron transporting layer is covered so as to be a thickness of 30 nm on the light-emitting layer. Then, an Al�Li alloy (Li content=0.5% by mass) serving as the negative electrodes is vapor deposited so as to be a thickness of 50 nm on the electron transporting layer formed by the Alq. The organic EL element is thus prepared.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 980 cd/m2 and whose peak is a wavelength of 600 nm, is observed.
Example 2 An organic EL element is prepared in the same way as in Example 1, except that the light-emitting layer is formed simultaneously by vapor depositing dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene, Alq, and rubrene such that the Alq is 94 molecules (94 mol) and the rubrene is 5 molecules (5 mol) to 1 molecule (1 mol) of the dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1500 cd/m2 and whose peak is a wavelength of 600 nm, is observed.
Example 3 An organic EL element is prepared in the same way as in Example 1, except that the dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene in Example 1 is replaced with 5,10-diphenyl-dinaphtho(2′:3′-3:4) (2″:3″-8:9)pyrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1390 cd/m2 and whose peak is a wavelength of 630 nm, is observed.
Example 4 An organic EL element is prepared in the same way as in Example 2, except that the dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene in Example 2 is replaced with 5,10-diphenyl-dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 2010 cd/m2 and whose peak is a wavelength of 630 nm, is observed.
Example 5 An organic EL element is prepared in the same way as in Example 1, except that the dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene in Example 1 is replaced with 5,10-bis(phenylamino)dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1260 cd/m2 and whose peak is a wavelength of 650 nm, is observed.
Example 6 An organic EL element is prepared in the same way as in Example 2, except that the dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene in Example 2 is replaced with 5,10-bis(phenylamino)dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1700 cd/m2 and whose peak is a wavelength of 650 nm, is observed.
Example 7 An organic EL element is prepared in the same way as in Example 1, except that the dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene in Example 1 is replaced with 5,10-bis(diphenylamino)dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene, and Alq is not used in the light-emitting layer, and the thickness of the electron transporting layer is made to be 50 nm.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 6V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 650 cd/m2 and whose peak is a wavelength of 655 nm, is observed.
Example 8 An organic EL element is prepared in the same way as in Example 1, except that the dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene in Example 1 is replaced with 5,10-bis(diphenylamino)dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1300 cd/m2 and whose peak is a wavelength of 655 nm, is observed.
Example 9 An organic EL element is prepared in the same way as in Example 2, except that the dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene in Example 2 is replaced with 5,10-bis(diphenylamino)dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1820 cd/m2 and whose peak is a wavelength of 655 nm, is observed.
Example 10 An organic EL element is prepared in the same way as in Example 1, except that the dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene in Example 1 is replaced with 5,10-bis(diphenylamino)dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene, and the positive hole transporting layer is not formed, and the light-emitting layer is made to be a positive hole transporting and light-emitting layer having a thickness of 50 nm.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 6V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 380 cd/m2 and whose peak is a wavelength of 655 nm, is observed.
Example 11 An organic EL element is prepared in the same way as in Example 1, except that the dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene in Example 1 is replaced with 5,10-diphenyl-dinaphtho(2′:3′-3:4)(2″:3″-8:9)pyrene, and the electron transporting layer is not formed, and the light-emitting layer is made to be an electron transporting and light-emitting layer having a thickness of 30 nm.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 7V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 160 cd/m2 and whose peak is a wavelength of 630 nm, is observed.
Synthesis Example 5 Synthesis of Dibenzanthanthrene
Dibenzanthanthrene expressed by the following formula is synthesized in accordance with a publication (�Bericht�, No. 76, p. 329 (1943)). Synthesis Example 6 Synthesis of 7,15-diphenyl-dibenzanthanthrene
Dibenzanthanthrene is dissolved in carbon tetrachloride. While the resultant mixture is cooled, 1 mol equivalent of bromine is added thereto. The mixture is reacted for 4 hours and brominated. Thereafter, the mixture is purified in accordance with a usual method, and 7,15-dibromodibenzanthanthrene is obtained. 2 mol equivalent of phenylboronic acid [Ph�B(OH)2] (wherein �Ph� represents a phenyl group) is refluxed and reacted for twelve hours with the 7,15-dibromodibenzanthanthrene obtained in this way, in a xylene/2M sodium carbonate aqueous solution, by using 0.01 mol equivalent of tetraquis(triphenylphosphine)palladium (0) [Pd(PPh3)4] (where �Ph� represents a phenyl group) as a catalyst. Thereafter, the resultant mixture is purified in accordance with a usual method, and the 7,15-diphenyl-dibenzanthanthrene expressed by the following formula is synthesized. (Note that, in the formula, �Ph� represents a phenyl group.) Synthesis Example 7 Synthesis of 7,15-bis(phenylamino)dibenzanthanthrene
Dibenzanthanthrene is dissolved in carbon tetrachloride. While the resultant mixture is cooled, 1 mol equivalent of bromine is added thereto. The mixture is reacted for 4 hours and brominated. Thereafter, the mixture is purified in accordance with a usual method, and 7,15-dibromodibenzanthanthrene is obtained. Phenylamine, potassium carbonate, and copper powder are added to the 7,15-dibromodibenzanthanthrene obtained in this way, and the mixture is reacted for 30 hours at 200� C. After the reaction solution is diluted with water, the reactant is eluted with chloroform. Thereafter, the resultant substance is purified in accordance with a usual method, and the 7,15-bis(phenylamino)dibenzanthanthrene represented by the following formula is synthesized. (Note that, in the formula, �Ph� represents a phenyl group.) Synthesis Example 8 Synthesis of 7,15-bis(diphenylamino)dibenzanthanthrene
Dibenzanthanthrene is dissolved in carbon tetrachloride. While the resultant mixture is cooled, 1 mol equivalent of bromine is added thereto. The mixture is reacted for 4 hours and brominated. Thereafter, the mixture is purified in accordance with a usual method, and 7,15-dibromodibenzanthanthrene is obtained. Diphenylamine, potassium carbonate, and copper powder are added to the 7,15-dibromodibenzanthanthrene obtained in this way, and the mixture is reacted for 30 hours at 200� C. After the reaction solution is diluted with water, the reactant is eluted with chloroform. Thereafter, the resultant substance is purified in accordance with a usual method, and the 7,15-bis(diphenylamino)dibenzanthanthrene represented by the following formula is synthesized. (Note that, in the formula, �Ph� represents a phenyl group.) Example 12 A laminated-type organic EL element using dibenzanthanthrene in the light-emitting layer is prepared as follows. Namely, a glass substrate, on which ITO electrodes are formed as positive electrodes, is washed with water, acetone and isopropyl alcohol. Using a vacuum vapor deposition device (degree of vacuum=1�10−6 Torr (1.3�10−4 Pa), substrate temperature=room temperature), TPD serving as a positive hole transporting layer is covered on the ITO electrodes so as to be a thickness of 50 nm. Next, a light-emitting layer having a thickness of 20 nm is formed by simultaneous vapor depositing, on the positive hole transporting layer formed by the TPD, dibenzanthanthrene and Alq such that the Alq is 99 molecules (99 mol) to 1 molecule (1 mol) of the dibenzanthanthrene. Then, Alq serving as an electron transporting layer is covered so as to be a thickness of 30 nm on the light-emitting layer. Then, an Al�Li alloy (Li content=0.5% by mass) serving as the negative electrodes is vapor deposited so as to be a thickness of 50 nm on the electron transporting layer formed by the Alq. The organic EL element is thus prepared.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 790 cd/m2 and whose peak is a wavelength of 620 nm, is observed.
Example 13 An organic EL element is prepared in the same way as in Example 12, except that the light-emitting layer is formed by simultaneous vapor depositing dibenzanthanthrene, Alq and rubrene such that the Alq is 94 molecules (94 mol) and the rubrene is 5 molecules (5 mol) with respect to 1 molecule (1 mol) of the dibenzanthanthrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1380 cd/m2 and whose peak is a wavelength of 620 nm, is observed.
Example 14 An organic EL element is prepared in the same way as in Example 12, except that the dibenzanthanthrene in Example 12 is replaced with 7,15-diphenyl-dibenzanthanthrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1450 cd/m2 and whose peak is a wavelength of 650 nm, is observed.
Example 15 An organic EL element is prepared in the same way as in Example 13, except that the dibenzanthanthrene in Example 13 is replaced with 7,15-diphenyl-dibenzanthanthrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 2240 cd/m2 and whose peak is a wavelength of 650 nm, is observed.
Example 16 An organic EL element is prepared in the same way as in Example 12, except that the dibenzanthanthrene in Example 12 is replaced with 7,15-bis(phenylamino)-dibenzanthanthrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1060 cd/m2 and whose peak is a wavelength of 660 nm, is observed.
Example 17 An organic EL element is prepared in the same way as in Example 13, except that the dibenzanthanthrene in Example 13 is replaced with 7,15-bis(phenylamino)-dibenzanthanthrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1410 cd/m2 and whose peak is a wavelength of 660 nm, is observed.
Example 18 An organic EL element is prepared in the same way as in Example 12, except that the dibenzanthanthrene in Example 12 is replaced with 7,15-bis(diphenylamino)-dibenzanthanthrene, Alq is not used in the light-emitting layer, and the thickness of the electron transporting layer is made to be 50 nm.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 6V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 550 cd/m2 and whose peak is a wavelength of 670 nm, is observed.
Example 19 An organic EL element is prepared in the same way as in Example 12, except that the dibenzanthanthrene in Example 12 is replaced with 7,15-bis(diphenylamino)-dibenzanthanthrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1100 cd/m2 and whose peak is a wavelength of 670 nm, is observed.
Example 20 An organic EL element is prepared in the same way as in Example 13, except that the dibenzanthanthrene in Example 13 is replaced with 7,15-bis(diphenylamino)-dibenzanthanthrene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1410 cd/m2 and whose peak is a wavelength of 670 nm, is observed.
Example 21 An organic EL element is prepared in the same way as in Example 12, except that the dibenzanthanthrene in Example 12 is replaced with 7,15-bis(diphenylamino)-dibenzanthanthrene, the positive hole transporting layer is not formed, and the light-emitting layer is made to be a positive hole transporting and light-emitting layer of a thickness of 50 nm.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 6V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 300 cd/m2 and whose peak is a wavelength of 670 nm, is observed.
Example 22 An organic EL element is prepared in the same way as in Example 12, except that the dibenzanthanthrene in Example 12 is replaced with 7,15-diphenyl-dibenzanthanthrene, the electron transporting layer is not formed, and the light-emitting layer is made to be an electron transporting and light-emitting layer of a thickness of 30 nm.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 7V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 190 cd/m2 and whose peak is a wavelength of 650 nm, is observed.
Synthesis Example 9 Synthesis of 6,13-diphenyl-naphthacenonaphthacene
Naphthacenonaphthacene (Chemical Abstract Service (CAS) Registry Number 180-50-1) is dissolved in carbon tetrachloride. While the resultant mixture is cooled, 1 mol equivalent of bromine is added thereto. The mixture is reacted for 4 hours and brominated. Thereafter, the mixture is purified in accordance with a usual method, and 6,13-dibromonaphthacenonaphthacene is obtained. 2 mol equivalent of phenylboronic acid [Ph�B(OH)2] (where �Ph� represents a phenyl group) is refluxed and reacted for 12 hours with the 6,13-dibromonaphthacenonaphthacene obtained in this way, in a xylene/2M sodium carbonate aqueous solution, by using 0.01 mol equivalent of tetraquis(triphenylphosphine)palladium (0) [Pd(PPh3)4] (where �Ph� represents a phenyl group) as a catalyst. Thereafter, the resultant mixture is purified in accordance with a usual method, and the 6,13-diphenyl-naphthacenonaphthacene expressed by the following formula is synthesized. (Note that, in the formula, �Ph� represents a phenyl group.) Synthesis Example 10 Synthesis of 6,13-bis(phenylamino)naphthacenonaphthacene
Naphthacenonaphthacene is dissolved in carbon tetrachloride. While the resultant mixture is cooled, 1 mol equivalent of bromine is added thereto. The mixture is reacted for 4 hours and brominated. Thereafter, the mixture is purified in accordance with a usual method, and 6,13-dibromonaphthacenonaphthacene is obtained. Phenylamine, potassium carbonate, and copper powder are added to the 6,13-dibromonaphthacenonaphthacene obtained in this way, and the mixture is reacted for 30 hours at 200� C. After the reaction solution is diluted with water, the reactant is eluted with chloroform. Thereafter, the resultant substance is purified in accordance with a usual method, and the 6,13-bis(phenylamino)naphthacenonaphthacene represented by the following formula is synthesized. (Note that, in the formula, �Ph� represents a phenyl group.) Synthesis Example 11 Synthesis of 6,13-bis(diphenylamino)naphthacenonaphthacene
Naphthacenonaphthacene is dissolved in carbon tetrachloride. While the resultant mixture is cooled, 1 mol equivalent of bromine is added thereto. The mixture is reacted for 4 hours and brominated. Thereafter, the mixture is purified in accordance with a usual method, and 6,13-dibromonaphthacenonaphthacene is obtained. Diphenylamine, potassium carbonate, and copper powder are added to the 6,13-dibromonaphthacenonaphthacene obtained in this way, and the mixture is reacted for 30 hours at 200� C. After the reaction solution is diluted with water, the reactant is eluted with chloroform. Thereafter, the resultant substance is purified in accordance with a usual method, and the 6,13-bis(diphenylamino)naphthacenonaphthacene represented by the following formula is synthesized. (Note that, in the formula, �Ph� represents a phenyl group.) Example 23 A laminated-type organic EL element using naphthacenonaphthacene in the light-emitting layer is prepared as follows. Namely, a glass substrate, on which ITO electrodes are formed as positive electrodes, is washed with water, acetone and isopropyl alcohol. Using a vacuum vapor deposition device (degree of vacuum=1�10−6 Torr (1.3�10−4 Pa), substrate temperature=room temperature), TPD serving as a positive hole transporting layer is covered on the ITO electrodes so as to be a thickness of 50 nm. Next, a light-emitting layer having a thickness of 20 nm is formed by simultaneously vapor depositing, on the positive hole transporting layer formed by the TPD, naphthacenonaphthacene and Alq such that the Alq is 99 molecules (99 mol) to 1 molecule (1 mol) of the naphthacenonaphthacene. Then, Alq serving as an electron transporting layer is covered so as to be a thickness of 30 nm on the light-emitting layer. Then, an Al�Li alloy (Li content=0.5% by mass) serving as the negative electrodes is vapor deposited so as to be a thickness of 50 nm on the electron transporting layer formed by the Alq. The organic EL element is thus prepared.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 820 cd/m2 and whose peak is a wavelength of 600 nm, is observed.
Example 24 An organic EL element is prepared in the same way as in Example 23, except that the light-emitting layer is formed by simultaneously vapor depositing naphthacenonaphthacene, Alq and rubrene such that the Alq is 94 molecules (94 mol) and the rubrene is 5 molecules (5 mol) with respect to 1 molecule (1 mol) of the naphthacenonaphthacene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1400 cd/m2 and whose peak is a wavelength of 600 nm, is observed.
Example 25 An organic EL element is prepared in the same way as in Example 23, except that the naphthacenonaphthacene in Example 23 is replaced with 6,13-diphenyl-naphthacenonaphthacene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1500 cd/m2 and whose peak is a wavelength of 630 nm, is observed.
Example 26 An organic EL element is prepared in the same way as in Example 24, except that the naphthacenonaphthacene in Example 24 is replaced with 6,13-diphenyl-naphthacenonaphthacene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 2300 cd/m2 and whose peak is a wavelength of 630 nm, is observed.
Example 27 An organic EL element is prepared in the same way as in Example 23, except that the naphthacenonaphthacene in Example 23 is replaced with 6,13-bis(phenylamino)-naphthacenonaphthacene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1100 cd/m2 and whose peak is a wavelength of 650 nm, is observed.
Example 28 An organic EL element is prepared in the same way as in Example 24, except that the naphthacenonaphthacene in Example 24 is replaced with 6,13-bis(phenylamino)-naphthacenonaphthacene.
Example 29 An organic EL element is prepared in the same way as in Example 23, except that the naphthacenonaphthacene in Example 23 is replaced with 6,13-bis(diphenylamino)-naphthacenonaphthacene, and Alq is not used in the light-emitting layer, and the thickness of the electron transporting layer is made to be 50 nm.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 6V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 600 cd/m2 and whose peak is a wavelength of 655 nm, is observed.
Example 30 An organic EL element is prepared in the same way as in Example 23, except that the naphthacenonaphthacene in Example 23 is replaced with 6,13-bis(diphenylamino)-naphthacenonaphthacene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1150 cd/m2 and whose peak is a wavelength of 655 nm, is observed.
Example 31 An organic EL element is prepared in the same way as in Example 24, except that the naphthacenonaphthacene in Example 24 is replaced with 6,13-bis(diphenylamino)-naphthacenonaphthacene.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 5V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 1450 cd/m2 and whose peak is a wavelength of 655 nm, is observed.
Example 32 An organic EL element is prepared in the same way as in Example 23, except that the naphthacenonaphthacene in Example 23 is replaced with 6,13-bis(diphenylamino)-naphthacenonaphthacene, and the positive hole transporting layer is not formed, and the light-emitting layer is made to be a positive hole transporting and light-emitting layer of a thickness of 50 nm.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 6V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 320 cd/m2 and whose peak is a wavelength of 655 nm, is observed.
Example 33 An organic EL element is prepared in the same way as in Example 23, except that the naphthacenonaphthacene in Example 23 is replaced with 6,13-diphenyl-naphthacenonaphthacene, and the electron transporting layer is not formed, and the light-emitting layer is made to be an electron transporting and light-emitting layer of a thickness of 30 nm.
When voltage is applied to the ITO electrodes (positive electrodes) and the Al�Li alloy (negative electrodes) of the prepared organic EL element, the emission of red light at a voltage of 7V or more is observed in the organic EL element. At an applied voltage of 10V, the emission of red light, whose light-emitting luminance is 220 cd/m2 and whose peak is a wavelength of 630 nm, is observed.
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