WO2012173011A1 - 有機電界発光素子、有機電界発光素子用の発光材料、並びに該素子を用いた発光装置、表示装置及び照明装置 - Google Patents
有機電界発光素子、有機電界発光素子用の発光材料、並びに該素子を用いた発光装置、表示装置及び照明装置 Download PDFInfo
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- WO2012173011A1 WO2012173011A1 PCT/JP2012/064430 JP2012064430W WO2012173011A1 WO 2012173011 A1 WO2012173011 A1 WO 2012173011A1 JP 2012064430 W JP2012064430 W JP 2012064430W WO 2012173011 A1 WO2012173011 A1 WO 2012173011A1
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Definitions
- the present invention relates to an organic electroluminescent element and a material compound for an organic electroluminescent element used therefor.
- the present invention also relates to a light emitting device, a display device or a lighting device using the organic electroluminescent element.
- Organic electroluminescent elements (hereinafter also referred to as “elements” and “organic EL elements”) are actively researched and developed because they can emit light with high luminance when driven at a low voltage.
- An organic electroluminescent element has an organic layer between a pair of electrodes, and electrons injected from the cathode and holes injected from the anode recombine in the organic layer, and the generated exciton energy is used for light emission. To do.
- Organic electroluminescence devices can be provided as devices having various emission wavelengths, and are expected to be applied to a wide range of applications because of their high response speed and relatively thin and light weight. Yes.
- the development of an organic electroluminescent device having high color purity and high luminous efficiency is important for application to full-color displays, and various development research results have been reported so far.
- Patent Document 1 describes that, as a fluorescent material, a material in which a ring is formed with a single bond and a methylene chain with respect to a condensed ring structure such as pyrene can emit light in a blue region and extend its lifetime. Has been.
- three types of compounds are used as blue dopants. According to Table 6, the chromaticity (0.14, 0.16) is described, and the maximum efficiency is described as 7.8 cd / A. Yes.
- a high-efficiency element with a wide gap (that is considered to be capable of blue light emission) can be obtained by using a molecule obtained by condensing benzofluorene with a ring as a light-emitting material.
- the spectrum of the fabricated device is disclosed, the wavelength is long and has a broad waveform, and the maximum emission wavelength is about 462 nm on average.
- the chromaticity of the organic electroluminescent elements described in Patent Document 1 and Patent Document 2 is still not sufficient as dark blue for display applications, and dark blue. It became clear that it was necessary to realize the light emission. Furthermore, it has been clarified that when these organic electroluminescent elements are used with the luminance being modulated, the chromaticity is changed with the modulation of the light emission intensity during driving.
- An object of the present invention is to solve the above problems. That is, the problem to be solved by the present invention is to provide an organic electroluminescent element that emits dark blue light and has a small change in chromaticity during luminance modulation.
- the present inventors have intensively studied for the purpose of providing an organic electroluminescent device that emits dark blue light and has a small chromaticity change during luminance modulation.
- the position of the pyrene skeleton at which the non-aromatic ring is condensed is referred to in Patent Document 1, in which the major axis of pyrene (1, 2, 3, 6, 7, 8) is referred to.
- the ring is preferably condensed in the (position) direction, the reason and the detailed mechanism thereof have not been particularly explained.
- Patent Document 2 an exemplary compound having a structure in which a non-aromatic ring is condensed so as to connect the major axis direction and the minor axis (positions 4, 5, 9, and 10) of two molecules of pyrene [ [0119]
- HOMO highest occupied orbital
- LUMO lowest unoccupied orbital
- the present inventors use a pyrene-based compound having a specific structure condensed in the minor axis direction as a light-emitting dopant for the device, which is dark blue light emission that could not be achieved conventionally, and at the time of luminance modulation It came to discover that an organic electroluminescent element with a small chromaticity change could be obtained.
- the skeleton of the compound having such a structure emits light at a short wavelength, and it is not necessary to introduce a substituent having a specific structure into the skeleton as in a conventionally known fluorescent light emitting material to shorten the wavelength. I understood it. That is, it has been found that the above-described problems can be solved by using a pyrene derivative having a specific structure, and the present invention described below has been provided.
- a substrate a pair of electrodes disposed on the substrate and including an anode and a cathode, and one or a plurality of organic layers disposed between the electrodes, the organic layer including a light emitting layer,
- the light emitting layer includes a host material and at least one light emitting material represented by the following general formula (1).
- n1 represents an integer of 0 to 8
- R 1 each independently represents a substituent substituted with a hydrogen atom of a pyrene skeleton (provided that when n1 is 2 or more, adjacent R 1 Except for the case where they are linked to each other to form a saturated or unsaturated ring)
- X is CR a R b (R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b are May form a 5- or 6-membered ring), NR c (R c represents a hydrogen atom or a substituent), O, S, SiR d R e (R d and R e are each independently Represents a hydrogen atom or a substituent, and R d and R e may together form a 5- or 6-membered ring.)
- a 1 to A 4 are each independently CR f ( R f is a hydrogen atom or a substituent, two R f the adjacent may be bonded
- Organic electroluminescent element [3] The organic electroluminescent element as described in [1] or [2], wherein in the general formula (1), R c represents a substituent. [4] In the general formula (1), X is CR a 'R b' (R a ', R b' are each independently an alkyl group, aryl group or heteroaryl group, and R a ' R b ′ may form a 5- or 6-membered ring jointly) or NR c ′ (R c ′ represents a substituent) [1] to [3] Organic electroluminescent element as described in any one of these.
- R 1 has an aryl group substituted with at least one N, N-diarylamino group or N, N-diarylamino group
- the organic electroluminescent element according to any one of to [4].
- R 2 to R 7 each independently represents a hydrogen atom or a substituent (provided that adjacent R 2 to R 7 are connected to each other to form a saturated or unsaturated ring).
- X is CR a R b (R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b may together form a 5- or 6-membered ring.) , NR c (R c represents a hydrogen atom or a substituent), O, S, SiR d R e (R d and R e each independently represents a hydrogen atom or a substituent, and R d and R e are And A 1 to A 4 each independently represents CR f (R f represents a hydrogen atom or a substituent, and two adjacent R's).
- X is CR a R b (R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b may together form a 5- or 6-membered ring), NR c (R c represents a hydrogen atom or a substituent), O, S, SiR d R e (R d , R e each independently represents a hydrogen atom or a substituent, and R d and R e together represent 5 Or a 6-membered ring may be formed).
- R 8 to R 11 each independently represents a hydrogen atom or a substituent, and two adjacent R 8 to R 11 may jointly form a saturated or unsaturated ring, but two or more R 8 to R 11 jointly form no more than two rings.
- R 12 and R 13 each independently represent a hydrogen atom or a substituent, and R 12 and R 13 may jointly form a 5- or 6-membered ring.
- Illumination device using the organic electroluminescent element according to any one of [1] to [15] [19] A luminescent material for an organic electroluminescent element represented by the following general formula (1).
- n1 represents an integer of 0 to 8
- R 1 each independently represents a substituent substituted with a hydrogen atom of a pyrene skeleton (provided that when n1 is 2 or more, adjacent R 1 Except for the case where they are linked to each other to form a saturated or unsaturated ring)
- X is CR a R b (R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b are May form a 5- or 6-membered ring), NR c (R c represents a hydrogen atom or a substituent), O, S, SiR d R e (R d and R e are each independently Represents a hydrogen atom or a substituent, and R d and R e may together form a 5- or 6-membered ring.)
- a 1 to A 4 are each independently CR f ( R f is a hydrogen atom or a substituent, two R f the adjacent may be bonded
- the organic electroluminescent element of the present invention emits dark blue light, and has an advantageous effect that a change in chromaticity during luminance modulation is small. Moreover, if the organic electroluminescent element material of the present invention is used, such an excellent organic electroluminescent element can be easily produced. Furthermore, the light-emitting device, display device, and lighting device of the present invention are advantageous in that power consumption is low, chromaticity is excellent, and chromaticity does not easily change during luminance modulation even when used in a device that requires luminance modulation. It is particularly suitable for display applications that have an effect and need to emit light with various luminances.
- a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
- the organic layer constituting the organic electroluminescent element includes a luminescent layer, and the luminescent layer contains a host material and at least one luminescent material represented by the following general formula (1). It is characterized by doing.
- n1 represents an integer of 0 to 8
- R 1 represents a substituent substituted on a hydrogen atom of the pyrene skeleton (provided that when n1 is 2 or more, adjacent R 1 are connected to each other). Unless it forms a saturated or unsaturated ring).
- X is CR a R b (R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b may together form a 5- or 6-membered ring), NR c (R c represents a hydrogen atom or a substituent), O, S, SiR d R e (R d , R e each independently represents a hydrogen atom or a substituent, and R d and R e together represent 5 Or a 6-membered ring may be formed).
- a 1 to A 4 each independently represent CR f (R f represents a hydrogen atom or a substituent, and two adjacent R f groups may form a saturated or unsaturated ring together, The above R f jointly forms no more than two rings.) Or N.
- the organic electroluminescent element of the present invention is a luminescent material for an organic electroluminescent element represented by the general formula (1) (hereinafter, a luminescent material represented by the general formula (1), a luminescent material of the present invention,
- the compound of the present invention is also used as a light emitting material.
- the applied voltage is different between low luminance and high luminance.
- the voltage dependency of the speed for transporting electrons and the voltage dependency of the speed for transporting holes are generally different. For this reason, it is considered that when the applied voltage is different, the relative difference between the electron transport speed and the hole transport speed is changed, and the position where recombination occurs in the light emitting layer is different.
- the organic electroluminescent element is a laminated body of a plurality of organic layers, the interference effect between the light emission reflected at the interface of each layer is different if the light emission position is different.
- the spectrum is broad or there are peaks other than the main peak, it is considered that the component on the long wave side is strengthened by interference and the chromaticity does not become constant.
- an organic electroluminescence device using the compound of the present invention as a luminescent material can emit blue light with a higher purity than that using a conventionally known similar compound. This is not bound by any theory, but it can be cited as a reason that the spectral shape is sharper in addition to the shortening of the wavelength that cannot be predicted from molecular orbital calculations. The spectral shape is sharp (a shape with a narrow half-value width and a small peak other than the main peak), etc., so that the change in chromaticity when driven at lower brightness and when driven at higher brightness is extremely small. I understood.
- shortening the wavelength by a substituent is synonymous with destabilization of the compound, and in many cases, the durability is lowered by cleavage of the substituent. Therefore, it has been demanded to shorten the wavelength of the mother skeleton or to reduce the spectrum.
- the mother skeleton itself contributes to the reduction in wavelength and the suppression of chromaticity change during luminance modulation. Therefore, in the luminescent material represented by the general formula (1), the substituent of the mother skeleton is hardly limited, and the above effect can be obtained.
- a specific substituent may be used to further improve wavelength reduction and suppression of chromaticity change during luminance modulation.
- the hydrogen atom in the description of the general formula (1) includes an isotope (deuterium atom and the like), and the atoms constituting the substituent further include the isotope.
- the substituent when the term “substituent” is used, the substituent may be further substituted.
- the term “alkyl group” in the present invention includes an alkyl group substituted with a fluorine atom (for example, trifluoromethyl group) and an alkyl group substituted with an aryl group (for example, triphenylmethyl group).
- alkyl group having 1 to 6 carbon atoms it means that all groups including substituted ones have 1 to 6 carbon atoms.
- X represents any of CR a R b , NR c , O, S, SiR d R e .
- CR a R b represents a constituent atom of the ring of the compound represented by the general formula (1), and R a and R b represent a hydrogen atom or a substituent bonded to the carbon atom.
- R a and R b may be the same or different.
- R a and R b may jointly form a 5- or 6-membered ring.
- the nitrogen atom is a constituent atom of the ring of the compound represented by the general formula (1), and R c represents a hydrogen atom or a substituent bonded to the nitrogen atom.
- R c is preferably a substituent.
- SiR d R e is a constituent atom of the ring of the compound represented by the general formula (1), and R d and R e represent a hydrogen atom or a substituent bonded to the silicon atom.
- R d and Re may be the same or different.
- R d and R e may jointly form a 5- or 6-membered ring.
- R a , R b , R d, and R e substituted on carbon atoms and substituents on silicon atoms
- substituent group A 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, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more
- Particularly preferably 0 to 10 carbon atoms such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc.
- an alkoxy group preferably having 1 to 30 carbon atoms, Preferably it has 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc.
- an aryloxy group preferably having 6 to 30 carbon atoms, More preferably, it has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms.
- heterocyclic oxy group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
- a heterocyclic oxy group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
- an acyl group preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms.
- Benzoyl, formyl, pivaloyl, etc. an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms such as methoxycarbonyl, ethoxy Carbonyl, etc.), an aryloxycarbonyl group (preferably having a carbon number)
- the number of carbon atoms is 7 to 30, more preferably 7 to 20, and particularly preferably 7 to 12, and examples thereof include phenyloxycarbonyl.
- An acyloxy group (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 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, and examples thereof include acetylamino, benzoylamino and the like, and alkoxycarbonylamino groups (preferably having 2-2 carbon atoms).
- an aryloxycarbonylamino group preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonyl And sulfonylamino groups (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).
- an aryloxycarbonylamino group preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonyl And sulfonylamino groups (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 having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenyl Sulfamoyl, etc.), carbamoyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, Phenylcarbamoyl etc.), alkylthio group ( Preferably, it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio, ethylthio, etc.), an arylthio group (preferably 6 to 30 carbon atoms).
- Rufinyl 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 methanesulfinyl and benzenesulfinyl. ), A ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid An amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide), a hydroxy group , Mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carb
- Is for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, And isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group and the like.
- a silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl).
- a aryloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy, triphenylsilyloxy, etc.), phosphoryl group (for example, A diphenylphosphoryl group, a dimethylphosphoryl group, etc.).
- These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.
- R a , R b , R d and R e are preferably each independently an alkyl group, aryl group, heteroaryl group, perfluoroalkyl group, alkoxy group or fluorine atom, more preferably an alkyl group, aryl group or hetero group.
- R a , R b , R d, and R e are each independently a linear, branched, or cyclic alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 14 carbon atoms; Is particularly preferably a heteroaryl group containing at least one of N, O and S as an atom, more preferably a linear or branched alkyl group having 1 to 6 carbon atoms. . From the viewpoint of ease of synthesis, R a and R b are preferably the same substituent. From the same viewpoint, R d and R e are preferably the same substituent.
- R c substituted on the nitrogen atom
- substituent group B examples include the following substituent group B.
- Substituent group B 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, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as propargy
- R c is preferably an alkyl group, a perfluoroalkyl group, an aryl group, or a fluorine atom.
- R c is a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 50 carbon atoms; 5 to 20 carbon atoms, and at least one of N, O and S as a hetero atom It is preferably any one of heteroaryl groups containing one.
- R c is preferably an aryl group having 6 to 14 carbon atoms; a heteroaryl group having 5 to 20 carbon atoms and containing at least one of N, O and S as a hetero atom.
- R a and R b , R d and R e may together form a 5- or 6-membered ring.
- the formed 5- or 6-membered ring may be a cycloalkyl ring, a cycloalkenyl ring, or a heterocyclic ring.
- Examples of the heterocycle include those containing 1 to 3 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom among the atoms constituting the ring.
- the formed 5- or 6-membered ring may have a substituent, and examples of the substituent on the carbon atom include the aforementioned substituent group A, and the substituent on the nitrogen atom includes the aforementioned substituent group B. It is done.
- X is preferably any one of CR a R b , NR c, and O, and any one of CR a R b or NR c is a viewpoint of emission color. Is more preferable.
- X is either CR a R b or NR c
- the formula (1) as in the general formula (2) described later, in the ring with R 2 and R 3 of the pyrene skeleton, and R 3 It is particularly preferred that the position next to R 2 on the opposite side is a hydrogen atom.
- X represents CR a ′ R b ′ (R a ′ and R b ′ each independently represents an alkyl group, an aryl group, or a heteroaryl group, and R a ′ and R b ′ And may form a 5- or 6-membered ring) or NR c ′ (R c ′ represents a substituent), more preferably CR a ′ R b ′. preferable.
- a 1 to A 4 each independently represent either CR f or N.
- the number of N is preferably 0 to 2, more preferably 0 or 1, and particularly preferably 0. That is, a preferred example is when A 1 to A 4 are all CR f .
- CR f is a constituent atom of the ring of the luminescent material represented by the general formula (1), and R f represents a hydrogen atom or a substituent bonded to the carbon atom. Examples of R f include the substituent group A described above.
- R f represents an alkyl group (more preferably a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms), an aryl group (more preferably an aryl group having 6 to 14 carbon atoms), a heteroaryl group (preferably a carbon number). 5 to 20, a heteroaryl group containing any one of N, O and S as a heteroatom), a disubstituted amino group (more preferably a dialkylamino group and a diarylamino group.
- the alkyl group and the aryl group A preferable range is the same as the preferable range of the alkyl group and aryl group in R 1 ), a halogeno group (preferably a fluoro group), a cyano group, and a nitro group.
- R f may be substituted with any one or more substituents, and the preferred range of the substituents in this case is the same as R 1 . More preferably, at least one R f is a substituent having any one of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a disubstituted amino group.
- a substituent having a group is particularly preferable, and an aryl group substituted with an N, N-diarylamino group or an alkyl group, or a substituent having an N, N-diarylamino group is particularly preferable. That is, it is more preferable that at least one R f is a group represented by the following general formula (Hp-1), (Hp-2) or (Hp-3).
- Ar 1 and Ar 2 each independently represents an aryl group.
- Ar 3 represents an arylene group
- Ar 4 and Ar 5 each independently represents an aryl group.
- Ar 6 represents an aryl group
- R h represents an alkyl group having 1 to 6 carbon atoms
- n h represents an integer of 1 to 4)
- Ar 1 , Ar 2 , Ar 4 and Ar 5 are each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group. Are preferred, and more preferred is substituted or unsubstituted phenyl.
- Ar 3 is preferably a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group, more preferably a substituted or unsubstituted phenylene, Particularly preferred is unsubstituted p-phenylene.
- Ar 6 is preferably a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group, and more preferably a substituted or unsubstituted phenylene group.
- R h is preferably any one of methyl, isopropyl, n-butyl, isobutyl, t-butyl, isopentyl, and neopentyl, and more preferably any of methyl, isopropyl, and t-butyl.
- two adjacent CR f may jointly form a saturated or unsaturated ring.
- Two or more R f jointly form no more than two rings.
- the formed ring is preferably a substituted or unsubstituted benzene ring, and is preferably an unsubstituted benzene ring. Examples of the case where R f forms a ring include the following partial structures, but the present invention is not limited to the following examples of partial structures.
- R 2 to R 7 in the following partial structure are the same as the explanation and preferred range of R 2 to R 7 in the general formula (2) described later, and the explanation of X in the following partial structure.
- the preferred range is the same as the explanation and preferred range of X in the general formula (1).
- N1 in the general formula (1) represents an integer of 0 to 8, preferably 0 to 7, more preferably 0 to 6, particularly preferably 1 to 4, and 1 or 2. More particularly preferred is 2 and even more preferred.
- each R 1 independently represents a substituent substituted with a hydrogen atom of the pyrene skeleton (provided that when n1 is 2 or more, adjacent R 1 are connected to each other to form a saturated or unsaturated ring). Except when forming).
- substituent include the above-mentioned substituent group A.
- an alkyl group (more preferably a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms), an aryl group (more preferably an aryl group having 6 to 14 carbon atoms), a heteroaryl group (preferably a carbon number of 5 To 20 and a heteroaryl group containing any one of N, O and S as a heteroatom), a disubstituted amino group (more preferably a dialkylamino group and a diarylamino group, and in this case, an alkyl group and an aryl group are preferred.
- the range is the same as the preferred range of the alkyl group and aryl group in R 1 ), a halogeno group (preferably a fluoro group), a cyano group, and a nitro group.
- R 1 may be substituted with any one or more substituents, and the preferred range of the substituents in this case is the same as R 1 .
- n1 is 2 or more, adjacent R 1 are not connected to each other to form a ring.
- the “ring” here includes both a case where an aromatic ring or a heterocyclic ring is newly condensed, or a case where a non-aromatic ring such as the following group (Het) is formed.
- At least one R 1 is a substituent having any of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a disubstituted amino group. It is particularly preferable to have a group, and it is particularly preferable to have an aryl group substituted with an N, N-diarylamino group or an N, N-diarylamino group. That is, at least one R 1 is more preferably a group represented by the general formula (Hp-1) or the general formula (Hp-2).
- the luminescent material represented by the general formula (1) is preferably a compound represented by the following general formula (2).
- R 2 to R 7 each independently represents a hydrogen atom or a substituent (except when adjacent R 2 to R 7 are connected to each other to form a saturated or unsaturated ring). ).
- X is CR a R b (R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b may together form a 5- or 6-membered ring), NR c (R c represents a hydrogen atom or a substituent), O, S, SiR d R e (R d , R e each independently represents a hydrogen atom or a substituent, and R d and R e together represent 5 Or a 6-membered ring may be formed).
- a 1 to A 4 each independently represent CR f (R f represents a hydrogen atom or a substituent, and two adjacent R f groups may form a saturated or unsaturated ring together, The above R f jointly forms two or less rings.) Or N.
- the explanation and preferred range of R 2 to R 7 in the general formula (2) are the same as the explanation and preferred range of R 1 in the general formula (1).
- the explanation and preferred range of X in the general formula (2) are the same as the explanation and preferred range of X in the explanation of the general formula (1).
- Description and the preferred range of A 1 ⁇ A 4 in the general formula (2) are the same as the preferable range as described in A 1 ⁇ A 4 in the description of general formula (1).
- the luminescent material represented by the general formula (1) is preferably a compound represented by the following general formula (3).
- R 2 to R 7 each independently represents a hydrogen atom or a substituent. However, the case where adjacent R 2 to R 7 are connected to each other to form a saturated or unsaturated ring is excluded.
- X is CR a R b (R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b may together form a 5- or 6-membered ring), NR c (R c represents a hydrogen atom or a substituent), O, S, SiR d R e (R d , R e each independently represents a hydrogen atom or a substituent, and R d and R e together represent 5 Or a 6-membered ring may be formed).
- R 8 to R 11 each independently represents a hydrogen atom or a substituent, and two adjacent R 8 to R 11 may jointly form a saturated or unsaturated ring, but two or more R 8 to R 11 jointly form no more than two rings.
- the explanation and preferred range of R 2 to R 7 in the general formula (3) are the same as the explanation and preferred range of R 1 in the general formula (1).
- the explanation and preferred range of X in the general formula (3) are the same as the explanation and preferred range of X in the explanation of the general formula (1).
- the explanation and preferred range of R 8 to R 11 in the general formula (3) are the same as the explanation and preferred range of R f in the explanation of the general formula (1).
- the luminescent material represented by the general formula (1) is preferably a compound represented by the following general formula (4).
- R 2 to R 7 each independently represents a hydrogen atom or a substituent. However, the case where adjacent R 2 to R 7 are connected to each other to form a saturated or unsaturated ring is excluded.
- R 8 to R 11 each independently represents a hydrogen atom or a substituent, and two adjacent R 8 to R 11 may jointly form a saturated or unsaturated ring, but two or more R 8 to R 11 jointly form no more than two rings.
- R 12 and R 13 each independently represent a hydrogen atom or a substituent, and R 12 and R 13 may jointly form a 5- or 6-membered ring.
- At least one of R 2 to R 11 preferably represents a substituent (other than a hydrogen atom or a deuterium atom), and R 3 , R 5 , R It is particularly preferred that at least one of 6 and R 10 represents a substituent, and it is particularly preferred that at least one of R 5 and R 10 represents a substituent.
- the explanation and preferred range of R 2 to R 7 in the general formula (4) are the same as the explanation and preferred range of R 1 in the general formula (1).
- the explanation and preferred range of R 8 to R 11 in the general formula (4) are the same as the explanation and preferred range of R f in the explanation of the general formula (1).
- the explanation and preferred range of R 12 and R 13 in the general formula (4) are the same as the explanation and preferred range of R a and R b in the explanation of the general formula (1).
- the maximum light emission wavelength of the organic electroluminescence device using the light emitting material represented by the general formula (1) is usually 400 nm to 480 nm.
- the thickness is preferably 420 nm to 470 nm, and more preferably 430 nm to 460 nm.
- the maximum emission wavelength of the organic electroluminescence device is about 430 nm to 460 nm, In particular, blue light emission with high color purity is obtained, which is preferable.
- the maximum emission wavelength of the organic electroluminescence device using the light emitting material represented by the general formula (1) is most preferably 440 nm or more and less than 455 nm from the viewpoint of obtaining blue light emission with high color purity.
- the light emitting material represented by the general formula (1) preferably has a molecular weight of 800 or less, more preferably 700 or less, and even more preferably 600 or less.
- the molecular weight By lowering the molecular weight, the sublimation temperature can be lowered, so that thermal decomposition of the compound during vapor deposition can be prevented. Also, the energy required for vapor deposition can be suppressed by shortening the vapor deposition time.
- the light emitting material represented by the general formula (1) can be synthesized by combining known reactions. Further, for example, it can be synthesized by the following scheme. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.
- the maximum light emission wavelength is preferably less than 455 nm, more preferably 400 nm or more and less than 455 nm, and 420 nm or more and less than 455 nm. Is particularly preferably 430 nm or more and less than 455 nm, and most preferably 440 nm or more and less than 455 nm.
- the organic electroluminescent element of the present invention comprises a substrate, a pair of electrodes disposed on the substrate and including an anode and a cathode, and one or a plurality of organic layers disposed between the electrodes. Includes a light emitting layer, and the light emitting layer includes a host material and at least one light emitting material represented by the general formula (1).
- the structure of the organic electroluminescent element of the present invention is not particularly limited. In FIG. 1, an example of a structure of the organic electroluminescent element of this invention is shown. 1 has an organic layer on a substrate 2 between a pair of electrodes (anode 3 and cathode 9).
- the element configuration, the substrate, the cathode, and the anode of the organic electroluminescence element are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.
- the preferable aspect of the organic electroluminescent element of this invention is demonstrated in detail in order of a board
- the organic electroluminescent element of the present invention has a substrate.
- the substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer.
- the organic electroluminescent element of the present invention is disposed on the substrate and has a pair of electrodes including an anode and a cathode.
- a pair of electrodes including an anode and a cathode.
- at least one of the pair of electrodes, the anode and the cathode is preferably transparent or translucent.
- the anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials.
- the anode is usually provided as a transparent anode.
- the cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element.
- the electrode material can be selected as appropriate.
- the organic electroluminescent element of the present invention has one or a plurality of organic layers disposed between the electrodes, and the organic layer includes a light emitting layer, and the light emitting layer includes a host material and at least one of the general formulas ( And a light emitting material represented by 1).
- the organic layer is formed on the entire surface or one surface of the transparent electrode or the semitransparent electrode.
- the organic layer includes a light emitting layer.
- the organic layer preferably includes a charge transport layer.
- the charge transport layer refers to a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element. Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer. If the charge transport layer is a hole injection layer, a hole transport layer, an electron block layer, or a light emitting layer, it is possible to manufacture an organic electroluminescent element with low cost and high efficiency.
- the compound represented by the general formula (1) is contained in at least one of the light emitting layers in one or more organic layers disposed between the electrodes of the organic electroluminescent element.
- the compound represented by the general formula (1-1) may be contained in the other organic layer of the organic electroluminescent element of the present invention unless it is contrary to the gist of the present invention.
- the organic layer other than the light emitting layer that may contain the compound represented by the general formula (1) includes a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge.
- a block layer (a hole block layer, an electron block layer, etc.) can be mentioned, preferably an exciton block layer, a charge block layer, an electron transport layer, an electron injection layer, more preferably an exciton block A layer, a charge blocking layer, or an electron transporting layer.
- the compound represented by the general formula (1) when the compound represented by the general formula (1) is contained in the light emitting layer, the compound represented by the general formula (1) may be contained in an amount of 0.1 to 100% by mass with respect to the total mass of the light emitting layer. Preferably, it is contained in an amount of 1 to 50% by mass, more preferably 2 to 20% by mass.
- the compound represented by the general formula (1) When the compound represented by the general formula (1) is contained in an organic layer other than the light emitting layer, the compound represented by the general formula (1) is contained in an amount of 70 to 100% by mass with respect to the total mass of the organic layer.
- the content is preferably 80 to 100% by mass, more preferably 90 to 100% by mass.
- each organic layer is formed by a dry film forming method such as a vapor deposition method or a sputtering method, a wet film forming method such as a transfer method, a printing method, a spin coating method, or a bar coating method (solution coating method). Any of these can be suitably formed.
- a dry film forming method such as a vapor deposition method or a sputtering method
- a wet film forming method such as a transfer method, a printing method, a spin coating method, or a bar coating method (solution coating method). Any of these can be suitably formed.
- the organic layer disposed between the pair of electrodes is formed by vapor deposition of a composition containing at least one compound represented by the general formula (1). .
- the light emitting layer receives holes from the anode, hole injection layer or hole transport layer and receives electrons from the cathode, electron injection layer or electron transport layer when an electric field is applied, and provides a field for recombination of holes and electrons. And a layer having a function of emitting light.
- the light emitting layer in the present invention is not necessarily limited to light emission by such a mechanism.
- the light emitting layer in the organic electroluminescent device of the present invention may be composed only of the light emitting material, or may be a mixed layer of a host material and the light emitting material.
- the kind of the light emitting material may be one kind or two kinds or more.
- the host material is preferably a charge transport material.
- the host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed.
- the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
- the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.
- the thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm from the viewpoint of external quantum efficiency. More preferably.
- the light emitting layer contains a compound represented by the general formula (1), and the compound represented by the general formula (1) is used as a light emitting material of the light emitting layer.
- the host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and is a compound that itself does not substantially emit light.
- substantially does not emit light means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
- the compound represented by the general formula (1) may be used as a host material of the light emitting layer.
- the compound represented by the general formula (1) is a light emitting material, but even in that case, the light emitting material different from the compound represented by the general formula (1) is used. Can be used in combination.
- the general formula ( A light emitting material different from the compound represented by 1) can be used for the light emitting layer.
- the light emitting material that can be used in the present invention is a fluorescent light emitting material.
- the light emitting layer in the present invention can contain two or more kinds of light emitting materials in order to improve color purity or broaden the light emission wavelength region.
- Examples of the fluorescent light-emitting material that can be used in the organic electroluminescence device of the present invention include, for example, paragraph numbers [0100] to [0164] of JP-A-2008-270736 and paragraph number [0088] of JP-A-2007-266458. ] To [0090], and the matters described in these publications can be applied to the present invention.
- the type of fluorescent light-emitting material that can be used in the present invention is not particularly limited.
- the light emitting layer in the organic electroluminescent element of the present invention may be composed only of a light emitting material, or may be a mixed layer of a host material and a light emitting material.
- the kind of the light emitting material may be one kind or two or more kinds.
- the host material is preferably a charge transport material.
- the host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed.
- the light emitting layer may contain a material that does not have charge transporting properties and does not emit light.
- the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.
- the host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and itself is a compound that does not substantially emit light.
- “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
- Examples of the host material that can be used in the organic electroluminescence device of the present invention include the following compounds. Pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, aryl Amines, amino-substituted chalcones, styrylanthracenes, fluorenones, hydrazones, stilbenes, silazanes, aromatic tertiary amine compounds, styrylamine compounds, porphyrin compounds, condensed aromatic hydrocarbon compounds (fluorene, naphthalene, phenanthrene, triphenylene, etc.) , Polys
- JP2010-111620A compounds described in [0081] and [0083] of JP2010-111620A can also be used.
- carbazole, dibenzothiophene, dibenzofuran, arylamine, a condensed ring aromatic hydrocarbon compound, and a metal complex are preferable, and a condensed ring aromatic hydrocarbon compound is particularly preferable because it is stable.
- the condensed aromatic hydrocarbon compound naphthalene compounds, anthracene compounds, phenanthrene compounds, triphenylene compounds and pyrene compounds are preferable, anthracene compounds and pyrene compounds are more preferable, and anthracene compounds are particularly preferable.
- the anthracene compounds those described in [0033] to [0064] of WO2010 / 134350 are particularly preferable, and examples thereof include compounds H-1 and H-2 described later.
- the host material contained in the light emitting layer preferably has a hydrocarbon condensed ring structure having 10 to 50 carbon atoms.
- the hydrocarbon condensed ring structure having 10 to 50 carbon atoms is preferably naphthalene, phenanthrene, benzo [c] phenanthrene, anthracene, pyrene, triphenylene and chrysene, more preferably naphthalene, phenanthrene, benzo [c] phenanthrene and anthracene, Is most preferred. That is, it is more preferable that the hydrocarbon condensed ring structure having 10 to 50 carbon atoms of the host material is an anthracene skeleton. Further, the hydrocarbon condensed ring structure having 10 to 50 carbon atoms is particularly preferably a compound composed only of carbon and hydrogen or deuterium.
- the host material that can be used in the light emitting layer in the organic electroluminescent device of the present invention may be a hole transporting host material or an electron transporting host material.
- the singlet minimum excitation energy (S 1 energy) in the film state of the host material is preferably higher than the S 1 energy of the light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable S 1 is greater than 0.1eV than S 1 of the light-emitting material of the host material, more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.
- the host material for S 1 in the film state of the host material will be quench S 1 is smaller than the light emission of the light emitting material larger S 1 is obtained from the luminescent material.
- the content of the host compound in the light emitting layer in the organic electroluminescence device of the present invention is not particularly limited, but is 15 with respect to the total mass of the compound forming the light emitting layer from the viewpoint of light emission efficiency and driving voltage. It is preferable that the content be ⁇ 95% by mass.
- the light emitting layer includes a plurality of types of host compounds including the compound represented by the general formula (1)
- the compound represented by the general formula (1) may be 50 to 99% by mass or less in the total host compounds. preferable.
- the organic electroluminescent element of the present invention may have other layers other than the light emitting layer.
- Other organic layers other than the light emitting layer that the organic layer may have include a hole injection layer, a hole transport layer, a block layer (hole block layer, exciton block layer, etc.), an electron transport layer, and the like. Is mentioned. Examples of the specific layer configuration include the following, but the present invention is not limited to these configurations.
- the organic electroluminescent element of the present invention preferably includes (A) at least one organic layer preferably disposed between the anode and the light emitting layer.
- Examples of the organic layer (A) preferably disposed between the anode and the light emitting layer include a hole injection layer, a hole transport layer, and an electron block layer from the anode side.
- the organic electroluminescent element of the present invention preferably includes (B) at least one organic layer preferably disposed between the cathode and the light emitting layer.
- Examples of the organic layer (B) preferably disposed between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, and a hole blocking layer from the cathode side.
- an example of a preferred embodiment of the organic electroluminescent device of the present invention is the embodiment described in FIG. 1, and as the organic layer, a hole injection layer 4, a hole transport layer 5, from the anode 3 side, In this embodiment, the light emitting layer 6, the hole blocking layer 7, and the electron transport layer 8 are laminated in this order.
- the organic layer a hole injection layer 4, a hole transport layer 5, from the anode 3 side
- the light emitting layer 6, the hole blocking layer 7, and the electron transport layer 8 are laminated in this order.
- other layers other than the light emitting layer which may be included in the organic electroluminescent element of the present invention will be described.
- A-1 Hole injection layer, hole transport layer
- the hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
- the light-emitting device of the present invention preferably includes at least one organic layer between the light-emitting layer and the anode.
- the organic layer includes the following general formula (Sa-1), general formula (Sb-1), general formula ( Among the compounds represented by Sc-1), it is preferable to contain at least one compound.
- X is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted group; Or an unsubstituted heteroarylene group having 2 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, wherein R S1 , R S2 , and R S3 each independently represent a hydrogen atom, An unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon group having 6 to 30 carbon atoms Aryloxy group, substituted or
- Ar S3 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
- R S8 and R S9 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon, Represents a heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, R S10 represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted An aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, R S11 and R S12.
- X represents a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon atom having 6 to It represents a 30 arylene group, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms.
- X is preferably a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, more preferably a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, and a substituted or unsubstituted naphthylene. More preferred is substituted or unsubstituted biphenylene.
- R S1 , R S2 and R S3 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon
- a cyclic group, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group is represented.
- Adjacent R S1 , R S2 and R S3 may be bonded to each other to form a saturated or unsaturated carbocycle.
- the saturated carbocycle or the unsaturated carbocycle include naphthalene, azulene, anthracene, fluorene, and phenalene.
- R S1 , R S2 and R S3 are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number.
- Ar S1 and Ar S2 each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
- Ar S1 and Ar S2 are preferably a substituted or unsubstituted phenyl group.
- R S4 , R S5 , R S6 and R S7 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number.
- saturated carbocycle or the unsaturated carbocycle examples include naphthalene, azulene, anthracene, fluorene, and phenalene.
- R S4 , R S5 , R S6 and R S7 are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted A condensed polycyclic group having 5 to 30 carbon atoms and a cyano group, more preferably a hydrogen atom.
- Ar S3 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
- Ar S3 is preferably a substituted or unsubstituted phenyl group.
- R S8 and R S9 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, It represents a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms.
- R S8 and R S9 are preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably a methyl group or a phenyl group. It is.
- R S10 represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, It represents an unsubstituted condensed polycyclic group having 5 to 30 carbon atoms.
- R S10 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and more preferably a phenyl group.
- R S11 and R S12 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon group having 6 to 30 aryl groups, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic rings having 2 to 30 carbon atoms, substituted or unsubstituted condensed polycyclic groups having 5 to 30 carbon atoms, It represents a hydroxy group, a cyano group, or a substituted or unsubstituted amino group.
- Adjacent R S11 and R S12 may be bonded to each other to form a saturated or unsaturated carbocycle.
- the saturated carbocycle or the unsaturated carbocycle include naphthalene, azulene, anthracene, fluorene, and phenalene.
- R S11 and R S12 are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon group having 5 to 30 carbon atoms.
- Ar S4 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
- Y S1 and Y S2 represent substituted or unsubstituted alkylene having 1 to 30 carbon atoms, or substituted or unsubstituted arylene having 6 to 30 carbon atoms.
- Y S1 and Y S2 are preferably substituted or unsubstituted arylene having 6 to 30 carbon atoms, and more preferably substituted or unsubstituted phenylene.
- n is an integer of 0 to 5, preferably 0 to 3, more preferably 0 to 2, and still more preferably 0.
- m is an integer of 0 to 5, preferably 0 to 3, more preferably 0 to 2, and still more preferably 1.
- the general formula (Sa-1) is preferably a compound represented by the following general formula (Sa-2).
- R S1 , R S2 and R S3 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted,
- An unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, a substituted or unsubstituted carbon atom having 5 to 30 represents a condensed polycyclic group, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group, and adjacent R S1 , R S2 , and R S3 are bonded to each other to form a saturated or unsaturated carbocyclic ring.
- Q Sa each independently represents a hydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or 6 to 30 carbon atoms.
- Aryloxy group, substituted or unsubstituted represents an aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted amino group.
- R S1 , R S2 and R S3 have the same meanings as those in formula (Sa-1), and preferred ranges are also the same.
- Q Sa is independently hydrogen atom, cyano group, fluorine atom, alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, aryloxy group having 6 to 30 carbon atoms, substituted Or an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms, or a substituted or unsubstituted amino group;
- Q Sa is preferably a hydrogen atom, a cyano group, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably A hydrogen
- the general formula (Sb-1) is preferably a compound represented by the following general formula (Sb-2).
- R S4 , R S5 , R S6 and R S7 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms.
- Substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, substituted or unsubstituted carbon Represents a condensed polycyclic group of 5 to 30, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group, and adjacent R S4 , R S5 , R S6 and R S7 are bonded to each other to form a saturated carbocyclic ring; Or an unsaturated carbocyclic ring, and Q Sb is a hydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, 6-30 aryloxy groups, substituted or Represents an un
- R S4 , R S5 , R S6 and R S7 have the same meanings as those in formula (Sb-1), and preferred ranges are also the same.
- Q Sa is a hydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted An aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms, or a substituted or unsubstituted amino group.
- Q Sa is preferably a hydrogen atom, a cyano group, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably A hydrogen atom and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, more preferably a hydrogen atom.
- the general formula (Sc-1) is preferably a compound represented by the following general formula (Sc-2).
- R S8 and R S9 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon, Represents a heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, R S10 represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted An aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, R S11 and R S12.
- R S11 and R S12 adjacent to each other may be bonded to each other to form a saturated or unsaturated carbocycle
- Q Sc is a hydrogen atom, a cyano group, a fluorine atom, or an alkoxy having 1 to
- R S8 , R S9 , R S10 , R S11 and R S12 have the same meanings as those in formula (Sc-1), and preferred ranges are also the same.
- Q Sc is a hydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted An aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted amino group.
- Q Sc is preferably a hydrogen atom, a cyano group, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably a hydrogen atom.
- the compound represented by the general formula (Sa-1), (Sb-1) or (Sc-1) can be synthesized by the method described in JP-A-2007-318101. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.
- the compound represented by the general formula (Sa-1), (Sb-1) or (Sc-1) is contained in an organic layer between the light emitting layer and the anode. Among them, it is more preferable that it be contained in a layer on the anode side adjacent to the light emitting layer, and a hole transport material contained in the hole transport layer is particularly preferable.
- the compound represented by the general formula (Sa-1), (Sb-1) or (Sc-1) is preferably contained in an amount of 70 to 100% by mass based on the total mass of the organic layer to be added, It is more preferable that 100 mass% is contained.
- the hole injection layer preferably contains an electron accepting dopant.
- an electron-accepting dopant may be any organic material or inorganic material as long as it can extract electrons from the doped material and generate radical cations.
- TCNQ tetracyanoquinodimethane
- F 4 -TCNQ tetrafluorotetracyanoquinodimethane
- molybdenum oxide and the like.
- the electron-accepting dopant in the hole injection layer is preferably contained in an amount of 0.01 to 50% by mass, preferably 0.1 to 40% by mass with respect to the total mass of the compound forming the hole injection layer.
- the content is more preferably 0.2 to 30% by mass.
- the electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side.
- an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
- the organic compound constituting the electron blocking layer for example, those mentioned as the hole transport material described above can be applied.
- the thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, and even more preferably 5 nm to 50 nm.
- the electron blocking 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.
- the material used for the electron blocking layer is preferably higher than the S 1 energy of the light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable S 1 is greater than 0.1eV than S 1 of the light-emitting material in the film state of the material used for the electron blocking layer, it is more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.
- the electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side.
- the electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
- As the electron transport material for example, a compound represented by the general formula (1) can be used.
- electron transport materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, benzimidazole derivatives, imidazopyridine derivatives.
- the thicknesses of the electron injection layer and the electron transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
- the thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
- the thickness of the electron injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.2 nm to 100 nm, and even more preferably from 0.5 nm to 50 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.
- the electron injection layer preferably contains an electron donating dopant.
- an electron donating dopant may be any organic material or inorganic material as long as it can give electrons to the doped material and generate radical anions.
- TTF tetrathiafulvalene
- TTT dithiaimidazole compounds
- TTT tetrathianaphthacene
- bis- [1,3 diethyl-2-methyl-1,2-dihydrobenzimidazolyl] lithium, cesium and the like.
- the electron donating dopant in the electron injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the electron injection layer. More preferably, the content is 0.5 to 30% by mass.
- the hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side.
- a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
- the S 1 energy in the film state of the organic compound constituting the hole blocking layer is higher than the S 1 energy of the light emitting material in order to prevent the energy transfer of excitons generated in the light emitting layer and not to reduce the light emission efficiency. It is preferable.
- a compound represented by the general formula (1) can be used as an example of the organic compound constituting the hole blocking layer.
- Examples of other organic compounds constituting the hole blocking layer other than the compound represented by the general formula (1) include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate ( Aluminum complexes such as aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as Balq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ( Phenanthroline derivatives such as 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)) and the like.
- BCP 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline
- the thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, still more preferably 5 nm to 50 nm.
- the hole blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.
- the material used for the hole blocking layer is preferably higher than the S 1 energy of the light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable S 1 is greater than 0.1eV than S 1 of the light-emitting material in the film state of the material used in the hole blocking layer, it is more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.
- the organic electroluminescent element of the present invention is preferably disposed between the (B) cathode and the light emitting layer.
- a material particularly preferably used for the material of the organic layer a compound represented by the general formula (1), a compound represented by the following general formula (P-1), and a compound represented by the following general formula (O-1) Can be mentioned.
- the compound represented by the general formula (O-1) and the compound represented by the general formula (P-1) will be described.
- the organic electroluminescent device of the present invention preferably includes at least one organic layer between the light emitting layer and the cathode, and the organic layer contains at least one compound represented by the following general formula (O-1). It is preferable from the viewpoint of device efficiency and driving voltage.
- the general formula (O-1) will be described below.
- R O1 represents an alkyl group, an aryl group, or each independently .A O1 ⁇ A O4 representing the heteroaryl group, the C-R A or .R A representing the nitrogen atom Represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R A may be the same or different, L O1 represents a divalent to hexavalent linking group comprising an aryl ring or a heteroaryl ring; N O1 represents an integer of 2 to 6.
- R O1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). It may have a substituent selected from group A.
- R O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group.
- a preferable substituent when the aryl group of R O1 has a substituent includes an alkyl group, an aryl group or a cyano group, more preferably an alkyl group or an aryl group, and still more preferably an aryl group.
- the aryl group of R O1 When the aryl group of R O1 has a plurality of substituents, the plurality of substituents may be bonded to each other to form a 5- or 6-membered ring.
- the aryl group of R O1 is preferably a phenyl group which may have a substituent selected from the substituent group A, more preferably a phenyl group which may be substituted with an alkyl group or an aryl group, More preferred is an unsubstituted phenyl group or 2-phenylphenyl group.
- a O1 to A O4 each independently represent C—R A or a nitrogen atom.
- 0 to 2 are preferably nitrogen atoms, more preferably 0 or 1 is a nitrogen atom.
- all of A O1 ⁇ A O4 is C-R A, or A O1 be a nitrogen atom, is preferably A O2 ⁇ A O4 is C-R A, A O1 be a nitrogen atom, A O2 ⁇ More preferably, A O4 is C—R A , A O1 is a nitrogen atom, A O2 to A O4 are C—R A , and R A is all hydrogen atoms.
- R A represents a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). It may have a substituent selected from the substituent group A.
- the plurality of R A may be the same or different.
- R A is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.
- L O1 represents a divalent to hexavalent linking group consisting of an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms).
- L O1 is preferably an arylene group, heteroarylene group, aryltriyl group, or heteroaryltriyl group, more preferably a phenylene group, a biphenylene group, or a benzenetriyl group, still more preferably a biphenylene group, Or it is a benzenetriyl group.
- L O1 may have a substituent selected from the aforementioned substituent group A, and the alkyl group, aryl group, or cyano group is preferred as the substituent when it has a substituent. Specific examples of L O1 include the following.
- n O1 represents an integer of 2 to 6, preferably an integer of 2 to 4, more preferably 2 or 3. n O1 is most preferably 3 in terms of device efficiency, and most preferably 2 in terms of device durability.
- the compound represented by the general formula (O-1) has a glass transition temperature (Tg) of 100 ° C. from the viewpoint of stable operation at high temperature storage, stable operation against high temperature driving, and heat generation during driving. It is preferably from ⁇ 300 ° C., more preferably from 120 ° C. to 300 ° C., further preferably from 120 ° C. to 300 ° C., and still more preferably from 140 ° C. to 300 ° C.
- the compound represented by the general formula (O-1) can be synthesized by the method described in JP-A No. 2001-335776. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.
- the compound represented by the general formula (O-1) is preferably contained in the organic layer between the light emitting layer and the cathode, but the cathode side layer adjacent to the light emitting layer is used. It is more preferable that it is contained.
- the compound represented by the general formula (O-1) is preferably contained in an amount of 70 to 100% by mass, and more preferably 85 to 100% by mass with respect to the total mass of the organic layer to be added.
- the organic electroluminescent element of the present invention preferably contains at least one organic layer between the light emitting layer and the cathode, and contains at least one compound represented by the following general formula (P) in the organic layer. Is preferable from the viewpoints of element efficiency and driving voltage. Below, general formula (P) is demonstrated.
- R P represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). These may have a substituent selected from the aforementioned substituent group A.
- nP represents an integer of 1 to 10, and when R P is plural, they may be the same or different.
- At least one of R P is a substituent represented by the following general formulas (P-1) to (P-3).
- R P1 to R P3 and R ′ P1 to R ′ P3 are an alkyl group (preferably having a carbon number of 1 to 8) and an aryl group (preferably having a carbon number of 6-30) or a heteroaryl group (preferably having 4 to 12 carbon atoms), which may have a substituent selected from the aforementioned substituent group A.
- n P1 and n P2 are 0 to Represents an integer of 4, and when R P1 to R P3 and R ′ P1 to R ′ P3 are plural, they may be the same or different, and L P1 to L P3 each represents a single bond, an aryl ring or a heteroaryl ring Represents one of divalent linking groups consisting of: * represents a bonding position with the anthracene ring of the general formula (P).
- a preferred substituent other than the substituents represented by (P-1) to (P-3) is an aryl group, more preferably any one of a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group. And more preferably a naphthyl group.
- R P1 to R P3 and R ′ P1 to R ′ P3 are preferably either aryl groups or heteroaryl groups, more preferably aryl groups, still more preferably phenyl groups, biphenyl groups, terphenyl groups, It is either a naphthyl group, most preferably a phenyl group.
- L P1 to L P3 are preferably a single bond or a divalent linking group comprising an aryl ring, more preferably a single bond, phenylene, biphenylene, terphenylene or naphthylene, still more preferably It is either a single bond, phenylene, or naphthylene.
- the compound represented by the general formula (P) can be synthesized by the methods described in WO2003 / 060956, WO2004 / 080975 and the like. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.
- the compound represented by the general formula (P) is preferably contained in the organic layer between the light emitting layer and the cathode, but may be contained in a layer adjacent to the cathode. More preferred.
- the compound represented by the general formula (P) is preferably contained in an amount of 70 to 100% by mass, and more preferably 85 to 100% by mass with respect to the total mass of the organic layer to be added.
- the entire organic electric field element may be protected by a protective layer.
- the protective layer the matters described in JP-A-2008-270736, paragraphs [0169] to [0170] can be applied to the present invention.
- the material for the protective layer may be inorganic or organic.
- the organic electroluminescent element of the present invention may be sealed entirely using a sealing container.
- the sealing container the matters described in paragraph [0171] of JP-A-2008-270736 can be applied to the present invention.
- the organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode.
- a direct current which may include an alternating current component as necessary
- the driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-290080, JP-A-7-134558, JP-A-8-234585, and JP-A-8-2441047.
- the driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.
- the external quantum efficiency of the organic electroluminescent element of the present invention is preferably 5% or more, more preferably 6% or more, and further preferably 7% or more.
- the value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency in the vicinity of 300 to 400 cd / m 2 when the device is driven at 20 ° C. Can do.
- the internal quantum efficiency of the organic electroluminescence device of the present invention is preferably 30% or more, more preferably 50% or more, and further preferably 70% or more.
- the internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a normal organic EL element, the light extraction efficiency is about 20%.
- the emission wavelength of the organic electroluminescent element of the present invention is the same as the maximum emission wavelength of the material for an organic electroluminescent element of the present invention, and is used for blue light emission among the three primary colors of light.
- blue light is emitted using the compound represented by the general formula (1) as a luminescent material.
- the organic electroluminescent element of the present invention can be suitably used for a display element, a display, a backlight, an electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication.
- a device that is driven in a region where light emission luminance is high such as a light emitting device, a lighting device, and a display device.
- the light emitting device of the present invention includes the organic electroluminescent element of the present invention. Next, the light emitting device of the present invention will be described with reference to FIG.
- the light emitting device of the present invention uses the organic electroluminescent element.
- FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention.
- the light emitting device 20 in FIG. 2 includes a transparent substrate (support substrate) 2, an organic electroluminescent element 10, a sealing container 16, and the like.
- the organic electroluminescent device 10 is configured by sequentially laminating an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2.
- a protective layer 12 is laminated on the cathode 9, and a sealing container 16 is provided on the protective layer 12 with an adhesive layer 14 interposed therebetween.
- a part of each electrode 3 and 9, a partition, an insulating layer, etc. are abbreviate
- the adhesive layer 14 a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.
- the use of the light-emitting device of the present invention is not particularly limited, and for example, it can be a display device such as a television, a personal computer, a mobile phone, and electronic paper in addition to a lighting device.
- FIG. 3 is a cross-sectional view schematically showing an example of the illumination device of the present invention.
- the illumination device 40 of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 are in contact with each other.
- the light scattering member 30 is not particularly limited as long as it can scatter light.
- the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31.
- a glass substrate can be preferably cited.
- the fine particles 32 transparent resin fine particles can be preferably exemplified.
- the glass substrate and the transparent resin fine particles known ones can be used. In such an illuminating device 40, when light emitted from the organic electroluminescent element 10 is incident on the light incident surface 30A of the scattering member 30, the incident light is scattered by the light scattering member 30, and the scattered light is emitted from the light emitting surface 30B. It is emitted as illumination light.
- the display device of the present invention includes the organic electroluminescent element of the present invention.
- Examples of the display device of the present invention include a display device such as a television, a personal computer, a mobile phone, and electronic paper.
- Synthesis Example 1 The compound represented by the general formula (1) can be synthesized by combining the methods described in this specification and other known reactions. Below, the typical example of the specific synthetic
- Synthesis Example 1 Synthesis of Compound 1 [Synthesis of Compound 1-b] In a 500 mL three-necked flask, compound 1-a (60.0 g, 187 mmol), diphenylamine (38.06 g, 225 mmol), copper iodide (18 mmol, 3.5 g), copper (37 mmol, 2.4 g), carbonic acid Potassium (374 mmol, 51.7 g) and 180 mL of diphenyl ether were added and heated at 200 ° C.
- reaction solution After dropping, the reaction solution is warmed to room temperature, then heated to 80 ° C. and heated for 3 hours.
- the reaction solution is neutralized with 1M aqueous ammonium chloride solution, and the organic layer is extracted with ethyl acetate.
- analogs 1-d ′ and 1-d ′′ of intermediate 1-d can be synthesized by reacting various disubstituted amines instead of reacting compound 1-a with diphenylamine. .
- Compounds 7 and 8 can be synthesized from 1-h ′ and 1-h ′′ according to the above synthesis method.
- the compound 12-a can be obtained by purification with
- Example 1 Preparation of organic electroluminescence device by vapor deposition
- a glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomat Co., Ltd., surface resistance 10 ⁇ / ⁇ ) is placed in a cleaning container, subjected to ultrasonic cleaning in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went.
- the following organic compound layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
- HAT-CN film thickness 10 nm
- NPD film thickness 30 nm
- Third layer H-1 and luminescent materials described in Table 1 (mass ratio 93: 7): film thickness 30 nm
- BAlq film thickness 30 nm
- HAT-CN represents the following structure.
- NPD represents the following structure.
- H-1 represents the following structure.
- BAlq represents Bis- (2-methyl-8-quinolinolato) -4- (phenyl-phenolate) -aluminum (III) having the following structure.
- Example 2 Preparation of coating solution for light emitting layer formation- Toluene (94.75% by mass) was mixed with the luminescent material 1 (0.25% by mass) and the host material ADN (5% by mass) to obtain a coating solution 1 for forming a luminescent layer.
- Luminescent layer forming coating solutions 2 and 3 were prepared in the same manner as the luminous layer forming coating solution 1 except that the luminous material 1 was changed to the luminous materials 3 and 6 in the luminous layer forming coating solution 1.
- ADN represents 9,10- (di-2-naphthyl) anthracene having the following structure.
- the light emitting layer forming coating solutions 1 to 6 were spin-coated (1,300 rpm, 30 seconds) so as to have a thickness of about 40 nm to obtain a light emitting layer.
- BAlq bis- (2-methyl-8-quinolinolato) -4- (phenyl-phenolato) -aluminum (III)
- BAlq bis- (2-methyl-8-quinolinolato) -4- (phenyl-phenolato) -aluminum (III)
- BAlq bis- (2-methyl-8-quinolinolato) -4- (phenyl-phenolato) -aluminum (III)
- LiF lithium fluoride
- organic electroluminescent elements 2-1 to 2-3 were produced.
- the obtained organic electroluminescent elements 2-1 to 2-3 all emitted dark blue light, and the change in chromaticity during luminance modulation was small.
- Example 11 A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomat Co., Ltd., surface resistance 10 ⁇ / ⁇ ) is placed in a cleaning container, subjected to ultrasonic cleaning in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. The following organic compound layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition. In addition, the vapor deposition rate in the following examples and comparative examples is 0.1 nm / second unless otherwise specified. The deposition rate was measured using a quartz resonator. The thickness of each layer below was measured using a quartz resonator.
- First layer HAT-CN: film thickness 10 nm
- Second layer HT-2: film thickness 35 nm
- Example 12 An organic electroluminescent element was produced in the same manner as in Example 11 except that the layer configuration was changed to the one shown below, and the same evaluation as in Example 11 was performed. The results are shown in Table 3.
- Third layer: H-2 and the light emitting materials described in Table 3 (mass ratio 95: 5): film thickness 25 nm
- Example 13 An organic electroluminescent element was produced in the same manner as in Example 11 except that the layer configuration was changed to the one shown below, and the same evaluation as in Example 11 was performed. The results are shown in Table 4.
- Third layer: H-1 and luminescent materials described in Table 4 (mass ratio 95: 5): film thickness 30 nm
- Example 14 An organic electroluminescent element was produced in the same manner as in Example 11 except that the layer configuration was changed to the one shown below, and the same evaluation as in Example 11 was performed. The results are shown in Table 5.
- Third layer: H-3 and the light emitting materials described in Table 5 (mass ratio 93: 7): film thickness 30 nm
- Example 15 An organic electroluminescent element was produced in the same manner as in Example 11 except that the layer configuration was changed to the one shown below, and the same evaluation as in Example 11 was performed. The results are shown in Table 6.
- Third layer: H-4 and luminescent materials described in Table 6 (mass ratio 93: 7): film thickness 30 nm
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Abstract
Description
また、公知文献2ではベンゾフルオレンを縮環拡大した分子を発光材料として用いることで、高効率であり、ギャップが広い(すなわち、青色発光が可能とも考えられる)素子が得られることが記載されている。この文献の実施例では作製された素子のスペクトルが開示されており、波長も長くブロードな波形であり、極大発光波長は平均して462nm程度であった。
本発明の目的は上記問題を解決することにある。すなわち、本発明が解決しようとする課題は、暗青色の発光であり、輝度変調時の色度変化が小さい有機電界発光素子を提供することにある。
ここで、ピレン骨格のどの位置に非芳香族環が縮環するかについて、特許文献1で言及しているが、該文献内ではピレンの長軸(1,2,3,6,7,8位)方向に縮環することが好ましいと記載されているものの、その理由およびその詳細なメカニズムは特に説明されていなかった。一方、特許文献2では、2分子のピレンの長軸方向と短軸(4,5,9,10位)方向を連結するように非芳香族環が縮環している構造の例示化合物を[0119]で用いていることからもわかる通り、ピレン骨格に対する縮環位置としてどの位置がよいかの記載はされていなかった。
このような状況のもと、発明者らが無置換のピレン分子について、ピレンの最高被占軌道(HOMO)および最低空軌道(LUMO)の配置の計算構造を求めた。その結果を下記図4に示す。図4より、ピレンの長軸方向と短軸方向に差異はないことがわかり、このことからもピレン骨格の縮環位置を変えることで電子的物性が変わることは想定し得なかったのが実情であった。
そのため、ピレン系化合物の構造を変化させて暗青色の発光であり、輝度変調時の色度変化が小さい有機電界発光素子用材料が得られるか否かについては、従来の知見から予想することは全くできていないのが実情であった。特に、従来、特許文献1に記載のように縮環ピレン系化合物として長軸方向に縮環している化合物が広く用いられており、特許文献1には長軸方向に縮環することが好ましいと記載されていたため、ピレンの縮環位置を大幅に変更することについては検討されていなかった。
すなわち、特定の構造を有するピレン誘導体を用いれば、上記の課題を解決することができることを見出して、以下に記載される本発明を提供するに至った。
[2] 前記一般式(1)において、Ra、Rb、RdおよびReがそれぞれ独立にアルキル基、アリール基およびヘテロアリール基のいずれかを表すことを特徴とする[1]に記載の有機電界発光素子。
[3] 前記一般式(1)において、Rcが置換基を表すことを特徴とする[1]または[2]に記載の有機電界発光素子。
[4] 前記一般式(1)において、XがCRa'Rb'(Ra'、Rb'はそれぞれ独立にアルキル基、アリール基、ヘテロアリール基のいずれかを表し、Ra'とRb'は共同して5または6員環を形成していてもよい。)またはNRc'(Rc'は置換基を表す。)を表すことを特徴とする[1]~[3]のいずれか一項に記載の有機電界発光素子。
[5] 前記一般式(1)において、R1が少なくとも1つのN,N-ジアリールアミノ基、または、N,N-ジアリールアミノ基で置換されたアリール基を有することを特徴とする[1]~[4]のいずれか一項に記載の有機電界発光素子。
[6] 前記一般式(1)で表される発光材料が、下記一般式(2)で表されることを特徴とする[1]~[5]のいずれか一項に記載の有機電界発光素子。
[7] 前記一般式(1)で表される発光材料が、下記一般式(3)で表されることを特徴とする[1]~[5]のいずれか一項に記載の有機電界発光素子。
XはCRaRb(Ra、Rbはそれぞれ独立に水素原子または置換基を表し、RaとRbは共同して5または6員環を形成していてもよい。)、NRc(Rcは水素原子または置換基を表す。)、O、S、SiRdRe(Rd、Reはそれぞれ独立に水素原子または置換基を表し、RdとReは共同して5または6員環を形成していてもよい。)のいずれかを表す。
R8~R11はそれぞれ独立に水素原子または置換基を表し、隣り合う2つのR8~R11は共同して飽和または不飽和の環を形成していてもよいが、2つ以上のR8~R11が共同して形成する環は2つ以下である。)
[8] 前記一般式(1)で表される発光材料が、下記一般式(4)で表されることを特徴とする[1]~[5]のいずれか一項に記載の有機電界発光素子。
R8~R11はそれぞれ独立に水素原子または置換基を表し、隣り合う2つのR8~R11は共同して飽和または不飽和の環を形成していてもよいが、2つ以上のR8~R11が共同して形成する環は2つ以下である。
R12、R13はそれぞれ独立に水素原子または置換基を表し、R12とR13は共同して5または6員環を形成していてもよい。)
[9] 前記一般式(4)において、R2~R11のうち少なくとも1つが置換基を表すことを特徴とする[8]のいずれか一項に記載の有機電界発光素子。
[10] 前記一般式(4)において、R5およびR10のうち少なくとも1つが置換基を表すことを特徴とする[8]に記載の有機電界発光素子。
[11] 前記一般式(1)で表される化合物の分子量が800以下であることを特徴とする[1]~[10]のいずれか一項に記載の有機電界発光素子。
[12] 前記発光層に含まれる前記ホスト材料が、炭素数10~50の炭化水素縮合環構造を有することを特徴とする[1]~[11]のいずれか一項に記載の有機電界発光素子。
[13] 前記ホスト材料の前記炭素数10~50の炭化水素縮合環構造がアントラセン骨格であることを特徴とする[12]に記載の有機電界発光素子。
[14] 前記発光層が真空蒸着プロセスにて形成されたことを特徴とする[1]~[13]のいずれか一項に記載の有機電界発光素子。
[15] 前記発光層が湿式プロセスにて形成されたことを特徴とする[1]~[13]のいずれか一項に記載の有機電界発光素子。
[16] [1]~[15]のいずれか一項に記載の有機電界発光素子を用いた発光装置。
[17] [1]~[15]のいずれか一項に記載の有機電界発光素子を用いた表示装置。
[18] [1]~[15]のいずれか一項に記載の有機電界発光素子を用いた照明装置
[19] 下記一般式(1)で表される有機電界発光素子用の発光材料。
本発明の有機電界発光素子は、有機電界発光素子を構成する有機層が発光層を含み、該発光層はホスト材料と、少なくとも1つの下記一般式(1)で表される発光材料とを含有することを特徴とする。
ここで、有機電界発光素子を駆動する場合、低輝度時と高輝度時では、印加電圧が異なる。有機層を用いる電界発光素子では電子を輸送する速度の電圧依存性とホールを輸送する速度の電圧依存性が異なるのが一般的である。このため、印加電圧が異なると電子の輸送速度とホールの輸送速度の相対差が変化し、発光層内で再結合が起こる位置が異なるものと考えられる。有機電界発光素子は複数の有機層の積層体であるため、発光位置が異なると各層の界面で反射する発光同士の干渉効果も異なる。ここでスペクトルがブロードであったり、主ピーク以外にピークが存在したりすると、長波側の成分が干渉によって強められ、色度が一定にならないと考えられる。
これに対し、本発明の化合物を発光材料として用いた有機電界発光素子は、従来公知の類似化合物を用いたものに比較して、純度の高い青色発光が得られる。これは、いかなる理論に拘泥するものでもないが、分子軌道計算からは予期できない短波長化に加えて、スペクトル形状がよりシャープになっていることが理由として挙げられる。スペクトル形状がシャープ(半値幅が狭く、主ピーク以外のピークが小さい形状)であることなどにより、さらに低輝度で駆動させた時と高輝度で駆動させた時の色度変化が極めて小さくなることがわかった。
これに対し、前記一般式(1)で表される有機電界発光素子用の発光材料は、その母骨格自体が、低波長化と、輝度変調時の色度変化の抑制に寄与している。そのため、前記一般式(1)で表される発光材料は、その母骨格の置換基はほとんど限定されず、上記効果を得ることができる。但し、本発明の好ましい態様においては、特定の置換基を用いて、さらに低波長化と輝度変調時の色度変化の抑制を改善してもよい。
本発明において、前記一般式(1)の説明における水素原子は同位体(重水素原子等)も含み、またさらに置換基を構成する原子は、その同位体も含んでいることを表す。
本発明において、「置換基」というとき、その置換基はさらに置換されていてもよい。例えば、本発明で「アルキル基」と言う時、フッ素原子で置換されたアルキル基(例えばトリフルオロメチル基)やアリール基で置換されたアルキル基(例えばトリフェニルメチル基)なども含むが、「炭素数1~6のアルキル基」と言うとき、置換されたものも含めた全ての基として炭素数が1~6であることを示す。
CRaRbは、その炭素原子が一般式(1)で表される化合物の環の構成原子となり、RaとRbはその炭素原子に結合する水素原子または置換基を表す。RaとRbは同一であっても異なっていてもよい。また、RaとRbは共同して5または6員環を形成していてもよい。
NRcは、その窒素原子が一般式(1)で表される化合物の環の構成原子となり、Rcはその窒素原子に結合する水素原子または置換基を表す。Rcは置換基であることが好ましい。
SiRdReはその珪素原子が一般式(1)で表される化合物の環の構成原子となり、RdとReはその珪素原子に結合する水素原子または置換基を表す。RdとReは同一であっても異なっていてもよい。また、RdとReは共同して5または6員環を形成していてもよい。
《置換基群A》
アルキル基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~10であり、例えばメチル、エチル、イソプロピル、t-ブチル、n-オクチル、n-デシル、n-ヘキサデシル、シクロプロピル、シクロペンチル、シクロヘキシルなどが挙げられる。)、アルケニル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばビニル、アリル、2-ブテニル、3-ペンテニルなどが挙げられる。)、アルキニル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばプロパルギル、3-ペンチニルなどが挙げられる。)、アリール基(好ましくは炭素数6~30、より好ましくは炭素数6~20、特に好ましくは炭素数6~12であり、例えばフェニル、p-メチルフェニル、ナフチル、アントラニルなどが挙げられる。)、アミノ基(好ましくは炭素数0~30、より好ましくは炭素数0~20、特に好ましくは炭素数0~10であり、例えばアミノ、メチルアミノ、ジメチルアミノ、ジエチルアミノ、ジベンジルアミノ、ジフェニルアミノ、ジトリルアミノなどが挙げられる。)、アルコキシ基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~10であり、例えばメトキシ、エトキシ、ブトキシ、2-エチルヘキシロキシなどが挙げられる。)、アリールオキシ基(好ましくは炭素数6~30、より好ましくは炭素数6~20、特に好ましくは炭素数6~12であり、例えばフェニルオキシ、1-ナフチルオキシ、2-ナフチルオキシなどが挙げられる。)、ヘテロ環オキシ基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばピリジルオキシ、ピラジルオキシ、ピリミジルオキシ、キノリルオキシなどが挙げられる。)、アシル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~12であり、例えばアセチル、ベンゾイル、ホルミル、ピバロイルなどが挙げられる。)、アルコキシカルボニル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~12であり、例えばメトキシカルボニル、エトキシカルボニルなどが挙げられる。)、アリールオキシカルボニル基(好ましくは炭素数7~30、より好ましくは炭素数7~20、特に好ましくは炭素数7~12であり、例えばフェニルオキシカルボニルなどが挙げられる。)、アシルオキシ基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばアセトキシ、ベンゾイルオキシなどが挙げられる。)、アシルアミノ基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばアセチルアミノ、ベンゾイルアミノなどが挙げられる。)、アルコキシカルボニルアミノ基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~12であり、例えばメトキシカルボニルアミノなどが挙げられる。)、アリールオキシカルボニルアミノ基(好ましくは炭素数7~30、より好ましくは炭素数7~20、特に好ましくは炭素数7~12であり、例えばフェニルオキシカルボニルアミノなどが挙げられる。)、スルホニルアミノ基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばメタンスルホニルアミノ、ベンゼンスルホニルアミノなどが挙げられる。)、スルファモイル基(好ましくは炭素数0~30、より好ましくは炭素数0~20、特に好ましくは炭素数0~12であり、例えばスルファモイル、メチルスルファモイル、ジメチルスルファモイル、フェニルスルファモイルなどが挙げられる。)、カルバモイル基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばカルバモイル、メチルカルバモイル、ジエチルカルバモイル、フェニルカルバモイルなどが挙げられる。)、アルキルチオ基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばメチルチオ、エチルチオなどが挙げられる。)、アリールチオ基(好ましくは炭素数6~30、より好ましくは炭素数6~20、特に好ましくは炭素数6~12であり、例えばフェニルチオなどが挙げられる。)、ヘテロ環チオ基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばピリジルチオ、2-ベンズイミゾリルチオ、2-ベンズオキサゾリルチオ、2-ベンズチアゾリルチオなどが挙げられる。)、スルホニル基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばメシル、トシルなどが挙げられる。)、スルフィニル基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばメタンスルフィニル、ベンゼンスルフィニルなどが挙げられる。)、ウレイド基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばウレイド、メチルウレイド、フェニルウレイドなどが挙げられる。)、リン酸アミド基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばジエチルリン酸アミド、フェニルリン酸アミドなどが挙げられる。)、ヒドロキシ基、メルカプト基、ハロゲン原子(例えばフッ素原子、塩素原子、臭素原子、ヨウ素原子)、シアノ基、スルホ基、カルボキシル基、ニトロ基、ヒドロキサム酸基、スルフィノ基、ヒドラジノ基、イミノ基、ヘテロ環基(芳香族ヘテロ環基も包含し、好ましくは炭素数1~30、より好ましくは炭素数1~12であり、ヘテロ原子としては、例えば窒素原子、酸素原子、硫黄原子、リン原子、ケイ素原子、セレン原子、テルル原子であり、具体的にはピリジル、ピラジニル、ピリミジル、ピリダジニル、ピロリル、ピラゾリル、トリアゾリル、イミダゾリル、オキサゾリル、チアゾリル、イソキサゾリル、イソチアゾリル、キノリル、フリル、チエニル、セレノフェニル、テルロフェニル、ピペリジル、ピペリジノ、モルホリノ、ピロリジル、ピロリジノ、ベンゾオキサゾリル、ベンゾイミダゾリル、ベンゾチアゾリル、カルバゾリル基、アゼピニル基、シロリル基などが挙げられる。)、シリル基(好ましくは炭素数3~40、より好ましくは炭素数3~30、特に好ましくは炭素数3~24であり、例えばトリメチルシリル、トリフェニルシリルなどが挙げられる。)、シリルオキシ基(好ましくは炭素数3~40、より好ましくは炭素数3~30、特に好ましくは炭素数3~24であり、例えばトリメチルシリルオキシ、トリフェニルシリルオキシなどが挙げられる。)、ホスホリル基(例えばジフェニルホスホリル基、ジメチルホスホリル基などが挙げられる。)が挙げられる。これらの置換基は更に置換されてもよく、更なる置換基としては、以上に説明した置換基群Aから選択される基を挙げることができる。また、置換基に置換した置換基は更に置換されてもよく、さらなる置換基としては、以上に説明した置換基群Aから選択される基を挙げることができる。また、置換基に置換した置換基に置換した置換基は更に置換されてもよく、さらなる置換基としては、以上に説明した置換基群Aから選択される基を挙げることができる。
Ra、Rb、RdおよびReはそれぞれ独立に、好ましくはアルキル基、アリール基、ヘテロアリール基、ペルフルオロアルキル基、アルコキシ基、フッ素原子であり、より好ましくはアルキル基、アリール基およびヘテロアリール基である。Ra、Rb、RdおよびReはそれぞれ独立に炭素数1~10の直鎖、分枝または環状のアルキル基;炭素数6~14のアリール基;炭素数5~20であり、ヘテロ原子としてN、OおよびSのいずれかを少なくとも1つ含むヘテロアリール基;のいずれかであることが特に好ましく、炭素数1~6の直鎖または分枝のアルキル基であることがより特に好ましい。また、合成容易性の観点からは、RaおよびRbが同じ置換基であることが好ましい。また、同様の観点からRdおよびReが同じ置換基であることが好ましい。
《置換基群B》
アルキル基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~10であり、例えばメチル、エチル、イソプロピル、t-ブチル、n-オクチル、n-デシル、n-ヘキサデシル、シクロプロピル、シクロペンチル、シクロヘキシルなどが挙げられる。)、アルケニル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばビニル、アリル、2-ブテニル、3-ペンテニルなどが挙げられる。)、アルキニル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばプロパルギル、3-ペンチニルなどが挙げられる。)、アリール基(好ましくは炭素数6~30、より好ましくは炭素数6~20、特に好ましくは炭素数6~12であり、例えばフェニル、p-メチルフェニル、ナフチル、アントラニルなどが挙げられる。)、シアノ基、ヘテロ環基(芳香族ヘテロ環基も包含し、好ましくは炭素数1~30、より好ましくは炭素数1~12であり、ヘテロ原子としては、例えば窒素原子、酸素原子、硫黄原子、リン原子、ケイ素原子、セレン原子、テルル原子であり、具体的にはピリジル、ピラジニル、ピリミジル、ピリダジニル、ピロリル、ピラゾリル、トリアゾリル、イミダゾリル、オキサゾリル、チアゾリル、イソキサゾリル、イソチアゾリル、キノリル、フリル、チエニル、セレノフェニル、テルロフェニル、ピペリジル、ピペリジノ、モルホリノ、ピロリジル、ピロリジノ、ベンゾオキサゾリル、ベンゾイミダゾリル、ベンゾチアゾリル、カルバゾリル基、アゼピニル基、シロリル基などが挙げられる。)これらの置換基は更に置換されてもよく、更なる置換基としては、前記置換基群Bから選択される基を挙げることができる。また、置換基に置換した置換基は更に置換されてもよく、さらなる置換基としては、以上に説明した置換基群Bから選択される基を挙げることができる。また、置換基に置換した置換基に置換した置換基は更に置換されてもよく、さらなる置換基としては、以上に説明した置換基群Bから選択される基を挙げることができる。
Rcは、好ましくはアルキル基、ペルフルオロアルキル基、アリール基、フッ素原子である。Rcは炭素数1~10の直鎖、分枝または環状のアルキル基;炭素数6~50のアリール基;炭素数5~20であり、ヘテロ原子としてN、OおよびSのいずれかを少なくとも1つ含むヘテロアリール基;のいずれかであることが好ましい。Rcは炭素数6~14のアリール基;炭素数5~20であり、ヘテロ原子としてN、OおよびSのいずれかを少なくとも1つ含むヘテロアリール基であることがより好ましい。
さらに、本発明では、XはCRa'Rb'(Ra'、Rb'はそれぞれ独立にアルキル基、アリール基、ヘテロアリール基のいずれかを表し、Ra'とRb'は共同して5または6員環を形成していてもよい。)またはNRc'(Rc'は置換基を表す。)であることが特に好ましく、CRa'Rb'であることがより特に好ましい。
CRfは、その炭素原子が一般式(1)で表される発光材料の環の構成原子となり、Rfはその炭素原子に結合する水素原子または置換基を表す。Rfとしては、上記の置換基群Aを挙げることができる。Rfは、アルキル基(より好ましくは炭素数1~10の直鎖、分岐または環状アルキル基)、アリール基(より好ましくは炭素数6~14のアリール基)、ヘテロアリール基(好ましくは炭素数5~20で、ヘテロ原子としてN、O、Sのいずれかを含むヘテロアリール基)、ジ置換アミノ基(より好ましくはジアルキルアミノ基、ジアリールアミノ基であり、この場合のアルキル基およびアリール基の好ましい範囲はR1におけるアルキル基およびアリール基の好ましい範囲と同様である)、ハロゲノ基(好ましくはフルオロ基)、シアノ基、ニトロ基を表す。
また、Rfは任意の1つ以上の置換基で置換されていてもよく、この場合の置換基の好ましい範囲はR1と同様である。
少なくとも1つのRfは、置換または無置換のアルキル基、置換または無置換のアリール基、および、ジ置換アミノ基のいずれかを有する置換基であることがより好ましく、置換アリール基またはジ置換アミノ基を有する置換基であることが特に好ましく、N,N-ジアリールアミノ基またはアルキル基で置換されたアリール基、あるいは、N,N-ジアリールアミノ基を有する置換基であることがより特に好ましい。すなわち、少なくとも1つのRfは、下記一般式(Hp-1)、(Hp-2)または(Hp-3)で表される基であることがより特に好ましい。
一般式(Hp-2)中、Ar3は置換または無置換のフェニレン基、あるいは、置換または無置換のナフチレン基であることが好ましく、置換または無置換のフェニレンであることがより好ましく、置換または無置換のp-フェニレンであることが特に好ましい。
一般式(Hp-3)中、Ar6は置換または無置換のフェニレン基、あるいは、置換または無置換のナフチレン基であることが好ましく、置換または無置換のフェニレン基であることがより好ましい。Rhはメチル、イソプロピル、n-ブチル、イソブチル、t-ブチル、イソペンチル、ネオペンチルのいずれかであることが好ましく、メチル、イソプロピル、t-ブチルのいずれかであることがより好ましい。
Rfが環を形成する場合の例としては下記の部分構造があげられるが、本発明は以下の部分構造の例によって限定されるものではない。また、下記の部分構造におけるR2~R7の説明および好ましい範囲は、後述する一般式(2)におけるR2~R7の説明および好ましい範囲と同様であり、下記の部分構造におけるXの説明および好ましい範囲は、前記一般式(1)におけるXの説明および好ましい範囲と同様である。
また、R1は任意の1つ以上の置換基で置換されていてもよく、この場合の置換基の好ましい範囲はR1と同様である。n1が2以上の場合、隣り合うR1は互いに連結して環を形成しない。ここでいう「環」とは、芳香環や複素環が新たに縮合する場合、もしくは下記群(Het)のような非芳香族環を形成する場合の両方を含む。
一般式(2)におけるR2~R7の説明と好ましい範囲は、一般式(1)におけるR1の説明と好ましい範囲と同じである。一般式(2)におけるXの説明と好ましい範囲は、一般式(1)の説明中におけるXの説明と好ましい範囲と同じである。一般式(2)におけるA1~A4の説明と好ましい範囲は、一般式(1)の説明中におけるA1~A4の説明と好ましい範囲と同じである。
XはCRaRb(Ra、Rbはそれぞれ独立に水素原子または置換基を表し、RaとRbは共同して5または6員環を形成していてもよい。)、NRc(Rcは水素原子または置換基を表す。)、O、S、SiRdRe(Rd、Reはそれぞれ独立に水素原子または置換基を表し、RdとReは共同して5または6員環を形成していてもよい。)のいずれかを表す。
R8~R11はそれぞれ独立に水素原子または置換基を表し、隣り合う2つのR8~R11は共同して飽和または不飽和の環を形成していてもよいが、2つ以上のR8~R11が共同して形成する環は2つ以下である。
一般式(3)におけるR2~R7の説明と好ましい範囲は、一般式(1)におけるR1の説明と好ましい範囲と同じである。一般式(3)におけるXの説明と好ましい範囲は、一般式(1)の説明中におけるXの説明と好ましい範囲と同じである。一般式(3)におけるR8~R11の説明と好ましい範囲は、一般式(1)の説明中におけるRfの説明と好ましい範囲と同じである。
R8~R11はそれぞれ独立に水素原子または置換基を表し、隣り合う2つのR8~R11は共同して飽和または不飽和の環を形成していてもよいが、2つ以上のR8~R11が共同して形成する環は2つ以下である。
R12、R13はそれぞれ独立に水素原子または置換基を表し、R12とR13は共同して5または6員環を形成していてもよい。
本発明の発光材料は、前記一般式(4)において、R2~R11のうち少なくとも1つが(水素原子、重水素原子以外の)置換基を表すことが好ましく、R3、R5、R6およびR10のうち少なくとも1つが置換基を表すことが特に好ましく、R5およびR10のうち少なくとも1つが置換基を表すことが特に好ましい。その他、一般式(4)におけるR2~R7の説明と好ましい範囲は、一般式(1)におけるR1の説明と好ましい範囲と同じである。一般式(4)におけるR8~R11の説明と好ましい範囲は、一般式(1)の説明中におけるRfの説明と好ましい範囲と同じである。一般式(4)におけるR12およびR13の説明と好ましい範囲は、一般式(1)の説明中におけるRaおよびRbの説明と好ましい範囲と同じである。
本発明の有機電界発光素子は、基板と、該基板上に配置され、陽極及び陰極を含む一対の電極と、該電極間に配置された1または複数の有機層とを有し、前記有機層は発光層を含み、該発光層はホスト材料と、少なくとも1つの前記一般式(1)で表される発光材料とを含むことを特徴とする。
本発明の有機電界発光素子の構成は、特に制限されることはない。図1に、本発明の有機電界発光素子の構成の一例を示す。図1の有機電界発光素子10は、基板2上に、一対の電極(陽極3と陰極9)の間に有機層を有する。
有機電界発光素子の素子構成、基板、陰極及び陽極については、例えば、特開2008-270736号公報に詳述されており、該公報に記載の事項を本発明に適用することができる。
以下、本発明の有機電界発光素子の好ましい態様について、基板、電極、有機層、保護層、封止容器、駆動方法、発光波長、用途の順で詳細に説明する。
本発明の有機電界発光素子は、基板を有する。
本発明で使用する基板としては、有機層から発せられる光を散乱又は減衰させない基板であることが好ましい。有機材料の場合には、耐熱性、寸法安定性、耐溶剤性、電気絶縁性、及び加工性に優れていることが好ましい。
本発明の有機電界発光素子は、前記基板上に配置され、陽極及び陰極を含む一対の電極を有する。
発光素子の性質上、一対の電極である陽極及び陰極のうち少なくとも一方の電極は、透明若しくは半透明であることが好ましい。
陽極は、通常、有機層に正孔を供給する電極としての機能を有していればよく、その形状、構造、大きさ等については特に制限はなく、発光素子の用途、目的に応じて、公知の電極材料の中から適宜選択することができる。前述のごとく、陽極は、通常透明陽極として設けられる。
陰極は、通常、有機層に電子を注入する電極としての機能を有していればよく、その形状、構造、大きさ等については特に制限はなく、発光素子の用途、目的に応じて、公知の電極材料の中から適宜選択することができる。
本発明の有機電界発光素子は、前記電極間に配置された1または複数の有機層を有し、前記有機層は発光層を含み、該発光層はホスト材料と、少なくとも1つの前記一般式(1)で表される発光材料とを含むことを特徴とする。
前記有機層は、特に制限はなく、有機電界発光素子の用途、目的に応じて適宜選択することができるが、前記透明電極上に又は前記半透明電極上に形成されるのが好ましい。この場合、有機層は、前記透明電極又は前記半透明電極上の全面又は一面に形成される。
有機層の形状、大きさ、及び厚み等については、特に制限はなく、目的に応じて適宜選択することができる。
以下、本発明の有機電界発光素子における、有機層の構成、有機層の形成方法、有機層を構成する各層の好ましい態様および各層に使用される材料について順に説明する。
本発明の有機電界発光素子では、前記有機層が発光層を含む。前記有機層が、電荷輸送層を含むことが好ましい。前記電荷輸送層とは、有機電界発光素子に電圧を印加した際に電荷移動が起こる層をいう。具体的には正孔注入層、正孔輸送層、電子ブロック層、発光層、正孔ブロック層、電子輸送層又は電子注入層が挙げられる。前記電荷輸送層が正孔注入層、正孔輸送層、電子ブロック層又は発光層であれば、低コストかつ高効率な有機電界発光素子の製造が可能となる。
但し、本発明の趣旨に反しない限りにおいて、前記一般式(1-1)で表される化合物は本発明の有機電界発光素子のその他の有機層に含有されていてもよい。前記一般式(1)で表される化合物を含有してもよい発光層以外の有機層としては、正孔注入層、正孔輸送層、電子輸送層、電子注入層、励起子ブロック層、電荷ブロック層(正孔ブロック層、電子ブロック層など)などを挙げることができ、好ましくは励起子ブロック層、電荷ブロック層、電子輸送層、電子注入層のいずれかであり、より好ましくは励起子ブロック層、電荷ブロック層、又は電子輸送層である。
本発明の有機電界発光素子において、各有機層は、蒸着法やスパッタ法等の乾式製膜法、転写法、印刷法、スピンコート法、バーコート法等の湿式製膜法(溶液塗布法)のいずれによっても好適に形成することができる。
本発明の有機電界発光素子は、前記一対の電極間に配置された有機層が、少なくとも一層の前記一般式(1)で表される化合物を含む組成物の蒸着により形成されていることが好ましい。
発光層は、電界印加時に、陽極、正孔注入層又は正孔輸送層から正孔を受け取り、陰極、電子注入層又は電子輸送層から電子を受け取り、正孔と電子の再結合の場を提供して発光させる機能を有する層である。但し、本発明における前記発光層は、このようなメカニズムによる発光に必ずしも限定されるものではない。
本発明の有機電界発光素子では、前記一般式(1)で表される化合物を発光材料とするが、その場合であっても前記一般式(1)で表される化合物とは別の発光材料を組み合わせて用いることが可能である。また、本発明の有機電界発光素子において、前記一般式(1)で表される化合物を発光層のホスト材料として使用する場合や、発光層以外の有機層に用いる場合にも、前記一般式(1)で表される化合物とは別の発光材料を発光層に用いることができる。
本発明において用いることができる発光材料は、蛍光発光材料である。また、本発明における発光層は、色純度を向上させたり、発光波長領域を広げたりするために、2種類以上の発光材料を含有することができる。
本発明の有機電界発光素子における発光層は、発光材料のみで構成されていてもよく、ホスト材料と発光材料の混合層とした構成でもよい。発光材料の種類は一種であっても二種以上であっても良い。ホスト材料は電荷輸送材料であることが好ましい。ホスト材料は一種であっても二種以上であってもよく、例えば、電子輸送性のホスト材料と正孔輸送性のホスト材料を混合した構成が挙げられる。更に、発光層中に電荷輸送性を有さず、発光しない材料を含んでいてもよい。
また、発光層は一層であっても二層以上の多層であってもよく、それぞれの層に同じ発光材料やホスト材料を含んでもよいし、層毎に異なる材料を含んでもよい。発光層が複数の場合、それぞれの発光層が異なる発光色で発光してもよい。
ホスト材料とは、発光層において主に電荷の注入、輸送を担う化合物であり、また、それ自体は実質的に発光しない化合物のことである。ここで「実質的に発光しない」とは、該実質的に発光しない化合物からの発光量が好ましくは素子全体での全発光量の5%以下であり、より好ましくは3%以下であり、更に好ましくは1%以下であることを言う。
ピロール、インドール、カルバゾール、アザインドール、アザカルバゾール、トリアゾール、オキサゾール、オキサジアゾール、ピラゾール、イミダゾール、チオフェン、ベンゾチオフェン、ジベンゾチオフェン、フラン、ベンゾフラン、ジベンゾフラン、ポリアリールアルカン、ピラゾリン、ピラゾロン、フェニレンジアミン、アリールアミン、アミノ置換カルコン、スチリルアントラセン、フルオレノン、ヒドラゾン、スチルベン、シラザン、芳香族第三級アミン化合物、スチリルアミン化合物、ポルフィリン系化合物、縮環芳香族炭化水素化合物(フルオレン、ナフタレン、フェナントレン、トリフェニレン等)、ポリシラン系化合物、ポリ(N-ビニルカルバゾール)、アニリン系共重合体、チオフェンオリゴマー、ポリチオフェン等の導電性高分子オリゴマー、有機シラン、カーボン膜、ピリジン、ピリミジン、トリアジン、イミダゾール、ピラゾール、トリアゾ-ル、オキサゾ-ル、オキサジアゾ-ル、フルオレノン、アントラキノジメタン、アントロン、ジフェニルキノン、チオピランジオキシド、カルボジイミド、フルオレニリデンメタン、ジスチリルピラジン、フッ素置換芳香族化合物、ナフタレンペリレン等の複素環テトラカルボン酸無水物、フタロシアニン、8-キノリノ-ル誘導体の金属錯体やメタルフタロシアニン、ベンゾオキサゾ-ルやベンゾチアゾ-ルを配位子とする金属錯体に代表される各種金属錯体及びそれらの誘導体(置換基や縮環を有していてもよい)等を挙げることができる。その他に、特開2010-111620の[0081]や[0083]に記載される化合物を用いることもできる。
これらのうち、カルバゾール、ジベンゾチオフェン、ジベンゾフラン、アリールアミン、縮環芳香族炭化水素化合物、金属錯体が好ましく、縮環芳香族炭化水素化合物が安定であるために特に好ましい。縮環芳香族炭化水素化合物としてはナフタレン系化合物、アントラセン系化合物、フェナントレン系化合物、トリフェニレン系化合物、ピレン系化合物が好ましく、アントラセン系化合物、ピレン系化合物がより好ましく、アントラセン系化合物が特に好ましい。アントラセン系化合物としては、WO2010/134350号公報の[0033]~[0064]に記載のものが特に好ましく、例えば後掲の化合物H-1やH-2を挙げることができる。
前記炭素数10~50の炭化水素縮合環構造は、ナフタレン、フェナントレン、ベンゾ[c]フェナントレン、アントラセン、ピレン、トリフェニレンおよびクリセンが好ましく、ナフタレン、フェナントレン、ベンゾ[c]フェナントレンおよびアントラセンがより好ましく、アントラセンが最も好ましい。すなわち、前記ホスト材料の前記炭素数10~50の炭化水素縮合環構造がアントラセン骨格であることがより好ましい。さらに、前記炭素数10~50の炭化水素縮合環構造は、炭素と水素または重水素のみで構成された化合物であることが特に好ましい。
ホスト材料の膜状態でのS1が発光材料のS1より小さいと発光を消光してしまうためホスト材料には発光材料より大きなS1が求められる。また、ホスト材料のS1が発光材料より大きい場合でも、両者のS1差が小さい場合には一部、発光材料からホスト材料への逆エネルギー移動が起こるため、効率低下や色純度低下、耐久性低下の原因となる。従って、S1が十分に大きく、化学的安定性及びキャリア注入・輸送性の高いホスト材料が求められる。
本発明の有機電界発光素子は、前記発光層以外のその他の層を有していてもよい。
前記有機層が有していてもよい前記発光層以外のその他の有機層として、正孔注入層、正孔輸送層、ブロック層(正孔ブロック層、励起子ブロック層など)、電子輸送層などが挙げられる。前記具体的な層構成として、下記が挙げられるが本発明はこれらの構成に限定されるものではない。
・陽極/正孔輸送層/発光層/電子輸送層/陰極、
・陽極/正孔輸送層/発光層/ブロック層/電子輸送層/陰極、
・陽極/正孔輸送層/発光層/ブロック層/電子輸送層/電子注入層/陰極、
・陽極/正孔注入層/正孔輸送層/発光層/ブロック層/電子輸送層/陰極、
・陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極、
・陽極/正孔注入層/正孔輸送層/発光層/ブロック層/電子輸送層/電子注入層/陰極、
・陽極/正孔注入層/正孔輸送層/ブロック層/発光層/ブロック層/電子輸送層/電子注入層/陰極。
本発明の有機電界発光素子は、(A)前記陽極と前記発光層との間に好ましく配置される有機層を少なくとも一層含むことが好ましい。前記(A)前記陽極と前記発光層との間に好ましく配置される有機層としては、陽極側から正孔注入層、正孔輸送層、電子ブロック層を挙げることができる。
本発明の有機電界発光素子は、(B)前記陰極と前記発光層との間に好ましく配置される有機層少なくとも一層含むことが好ましい。前記(B)前記陰極と前記発光層との間に好ましく配置される有機層としては、陰極側から電子注入層、電子輸送層、正孔ブロック層を挙げることができる。
具体的には、本発明の有機電界発光素子の好ましい態様の一例は、図1に記載される態様であり、前記有機層として、陽極3側から正孔注入層4、正孔輸送層5、発光層6、正孔ブロック層7及び電子輸送層8がこの順に積層されている態様である。
以下、これら本発明の有機電界発光素子が有していてもよい前記発光層以外のその他の層について、説明する。
まず、(A)前記陽極と前記発光層との間に好ましく配置される有機層について説明する。
正孔注入層、正孔輸送層は、陽極又は陽極側から正孔を受け取り陰極側に輸送する機能を有する層である。
前記一般式(Sa-1)中、Xは、置換または無置換の炭素数1~30のアルキレン基、置換または無置換の炭素数2~30のアルケニレン基、置換または無置換の炭素数6~30のアリーレン基、置換または無置換の炭素数2~30のヘテロアリーレン基、あるいは、置換または無置換の炭素数2~30の複素環を表す。Xとして好ましくは、置換または無置換の炭素数6~30のアリーレン基であり、より好ましくは、置換または無置換のフェニレン、置換または無置換のビフェニレン、および、置換または無置換のナフチレンであり、さらに好ましくは置換または無置換のビフェニレンである。
RS1、RS2、RS3は、各々独立に水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数1~30のアルコキシ基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数6~30のアリールオキシ基、置換または無置換の炭素数2~30の複素環、置換または無置換の炭素数5~30の縮合多環基、ヒドロキシ基、シアノ基、あるいは、置換または無置換のアミノ基を表す。隣接するRS1、RS2、RS3同士が互いに結合し、飽和炭素環または不飽和炭素環を形成してもよい。前記飽和炭素環または当該不飽和炭素環の例としては、ナフタレン、アズレン、アントラセン、フルオレン、フェナレンなどがある。RS1、RS2、RS3として好ましくは、水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数5~30の縮合多環基、および、シアノ基であり、より好ましくは水素原子である。
ArS1、ArS2は、各々独立に、置換または無置換の炭素数6~30のアリール基、あるいは、置換または無置換の炭素数2~30のヘテロアリール基を表す。ArS1、ArS2として好ましくは、置換または無置換のフェニル基である。
前記一般式(Sb-1)中、RS4、RS5、RS6およびRS7は、各々独立に水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数1~30のアルコキシ基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数6~30のアリールオキシ基、置換または無置換の炭素数2~30の複素環、または置換または無置換の炭素数5~30の縮合多環基、ヒドロキシ基、シアノ基、あるいは、置換または無置換のアミノ基を表す。隣接するRS4、RS5、RS6およびRS7同士が互いに結合し、飽和炭素環または不飽和炭素環を形成してもよい。前記飽和炭素環または当該不飽和炭素環の例としては、ナフタレン、アズレン、アントラセン、フルオレン、フェナレンなどがある。RS4、RS5、RS6およびRS7として好ましくは、水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数5~30の縮合多環基、および、シアノ基であり、より好ましくは水素原子である。
ArS3は、置換または無置換の炭素数6~30のアリール基、あるいは、置換または無置換の炭素数2~30のヘテロアリール基を表す。ArS3として好ましくは、置換または無置換のフェニル基である。
前記一般式(Sc-1)中、RS8およびRS9は各々独立に水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数2~30の複素環基、あるいは、置換または無置換の炭素数5~30の縮合多環基を表す。RS8およびRS9として好ましくは、置換または無置換の炭素数1~30のアルキル基、および、置換または無置換の炭素数6~30のアリール基であり、より好ましくは、メチル基およびフェニル基である。RS10は置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数2~30の複素環基、あるいは、置換または無置換の炭素数5~30の縮合多環基を表す。RS10として好ましくは置換または無置換の炭素数6~30のアリール基であり、より好ましくはフェニル基である。RS11およびRS12は、各々独立に水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数1~30のアルコキシ基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数6~30のアリールオキシ基、置換または無置換の炭素数2~30の複素環、置換または無置換の炭素数5~30の縮合多環基、ヒドロキシ基、シアノ基、あるいは、置換または無置換のアミノ基を表す。隣接するRS11およびRS12同士が互いに結合し、飽和炭素環または不飽和炭素環を形成してもよい。前記飽和炭素環または当該不飽和炭素環の例としては、ナフタレン、アズレン、アントラセン、フルオレン、フェナレンなどがある。RS11およびRS12として好ましくは、水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数5~30の縮合多環基、および、シアノ基であり、より好ましくは水素原子である。ArS4は、置換または無置換の炭素数6~30のアリール基、あるいは、置換または無置換の炭素数2~30のヘテロアリール基を表す。YS1、YS2は置換または無置換の炭素数1~30のアルキレン、あるいは、置換または無置換の炭素数6~30のアリーレンを表す。YS1、YS2として好ましくは、置換または無置換の炭素数6~30のアリーレンであり、より好ましくは置換または無置換のフェニレンである。nは0~5の整数であり、好ましくは0~3、より好ましくは0~2、さらに好ましくは0である。mは0~5の整数であり、好ましくは0~3、より好ましくは0~2、さらに好ましくは1である。
前記一般式(Sa-1)、(Sb-1)または(Sc-1)で表される化合物は、添加する有機層の全質量に対して70~100質量%含まれることが好ましく、85~100質量%含まれることがより好ましい。
電子ブロック層は、陰極側から発光層に輸送された電子が、陽極側に通りぬけることを防止する機能を有する層である。本発明において、発光層と陽極側で隣接する有機層として、電子ブロック層を設けることができる。
電子ブロック層を構成する有機化合物の例としては、例えば前述の正孔輸送材料として挙げたものが適用できる。
電子ブロック層の厚さとしては、1nm~500nmであるのが好ましく、3nm~100nmであるのがより好ましく、5nm~50nmであるのが更に好ましい。
電子ブロック層は、上述した材料の一種又は二種以上からなる単層構造であってもよいし、同一組成又は異種組成の複数層からなる多層構造であってもよい。
電子ブロック層に用いる材料は、前記発光材料のS1エネルギーより高いことが色純度、発光効率、駆動耐久性の点で好ましい。電子ブロック層に用いる材料の膜状態でのS1が発光材料のS1より0.1eV以上大きいことが好ましく、0.2eV以上大きいことがより好ましく、0.3eV以上大きいことが更に好ましい。
次に、前記(B)陰極と前記発光層との間に好ましく配置される有機層について説明する。
電子注入層、電子輸送層は、陰極又は陰極側から電子を受け取り陽極側に輸送する機能を有する層である。これらの層に用いる電子注入材料、電子輸送材料は低分子化合物であっても高分子化合物であってもよい。
電子輸送材料としては、例えば前記一般式(1)で表される化合物を用いることができる。その他の電子輸送材料としては、ピリジン誘導体、キノリン誘導体、ピリミジン誘導体、ピラジン誘導体、フタラジン誘導体、フェナントロリン誘導体、トリアジン誘導体、トリアゾール誘導体、オキサゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ベンゾイミダゾール誘導体、イミダゾピリジン誘導体、フルオレノン誘導体、アントラキノジメタン誘導体、アントロン誘導体、ジフェニルキノン誘導体、チオピランジオキシド誘導体、カルボジイミド誘導体、フルオレニリデンメタン誘導体、ジスチリルピラジン誘導体、ナフタレン、ペリレン等の芳香環テトラカルボン酸無水物、フタロシアニン誘導体、8-キノリノール誘導体の金属錯体やメタルフタロシアニン、ベンゾオキサゾールやベンゾチアゾールを配位子とする金属錯体に代表される各種金属錯体、シロールに代表される有機シラン誘導体、ナフタレン、アントラセン、フェナントレン、トリフェニレン、ピレン等の縮環炭化水素化合物等をから選ばれることが好ましく、ピリジン誘導体、ベンゾイミダゾール誘導体、イミダゾピリジン誘導体、金属錯体、縮環炭化水素化合物のいずれかであることがより好ましい。
電子輸送層の厚さとしては、1nm~500nmであるのが好ましく、5nm~200nmであるのがより好ましく、10nm~100nmであるのが更に好ましい。また、電子注入層の厚さとしては、0.1nm~200nmであるのが好ましく、0.2nm~100nmであるのがより好ましく、0.5nm~50nmであるのが更に好ましい。
電子注入層、電子輸送層は、上述した材料の1種又は2種以上からなる単層構造であってもよいし、同一組成又は異種組成の複数層からなる多層構造であってもよい。
正孔ブロック層は、陽極側から発光層に輸送された正孔が、陰極側に通りぬけることを防止する機能を有する層である。本発明において、発光層と陰極側で隣接する有機層として、正孔ブロック層を設けることができる。
正孔ブロック層を構成する有機化合物の膜状態でのS1エネルギーは、発光層で生成する励起子のエネルギー移動を防止し、発光効率を低下させないために、発光材料のS1エネルギーよりも高いことが好ましい。
正孔ブロック層を構成する有機化合物の例としては、例えば前記一般式(1)で表される化合物を用いることができる。
前記一般式(1)で表される化合物以外の、正孔ブロック層を構成するその他の有機化合物の例としては、アルミニウム(III)ビス(2-メチル-8-キノリナト)4-フェニルフェノレート(Aluminum (III)bis(2-methyl-8-quinolinato)4-phenylphenolate(Balqと略記する))等のアルミニウム錯体、トリアゾール誘導体、2,9-ジメチル-4,7-ジフェニル-1,10-フェナントロリン(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline(BCPと略記する))等のフェナントロリン誘導体、等が挙げられる。
正孔ブロック層の厚さとしては、1nm~500nmであるのが好ましく、3nm~100nmであるのがより好ましく、5nm~50nmであるのが更に好ましい。
正孔ブロック層は、上述した材料の一種又は二種以上からなる単層構造であってもよいし、同一組成又は異種組成の複数層からなる多層構造であってもよい。
正孔ブロック層に用いる材料は、前記発光材料のS1エネルギーより高いことが色純度、発光効率、駆動耐久性の点で好ましい。正孔ブロック層に用いる材料の膜状態でのS1が発光材料のS1より0.1eV以上大きいことが好ましく、0.2eV以上大きいことがより好ましく、0.3eV以上大きいことが更に好ましい。
本発明の有機電界発光素子は、前記(B)陰極と前記発光層との間に好ましく配置される有機層の材料に特に好ましく用いられる材料として、前記一般式(1)で表される化合物、下記一般式(P-1)で表される化合物および下記一般式(O-1)で表される化合物を挙げることができる。
以下、前記一般式(O-1)で表される化合物と、前記一般式(P-1)で表される化合物について説明する。
一般式(O-1)で表される化合物は、添加する有機層の全質量に対して70~100質量%含まれることが好ましく、85~100質量%含まれることがより好ましい。
RP1~RP3、R’P1~R’P3として、好ましくはアリール基、ヘテロアリール基のいずれかであり、より好ましくはアリール基であり、更に好ましくはフェニル基、ビフェニル基、ターフェニル基、ナフチル基のいずれかであり、最も好ましくはフェニル基である。
LP1~LP3として、好ましくは単結合、アリール環からなる二価の連結基のいずれかであり、より好ましくは単結合、フェニレン、ビフェニレン、ターフェニレン、ナフチレンのいずれかであり、更に好ましくは単結合、フェニレン、ナフチレンのいずれかである。
一般式(P)で表される化合物は、添加する有機層の全質量に対して70~100質量%含まれることが好ましく、85~100質量%含まれることがより好ましい。
本発明において、有機電界素子全体は、保護層によって保護されていてもよい。
保護層については、特開2008-270736号公報の段落番号〔0169〕~〔0170〕に記載の事項を本発明に適用することができる。なお、保護層の材料は無機物であっても、有機物であってもよい。
本発明の有機電界発光素子は、封止容器を用いて素子全体を封止してもよい。
封止容器については、特開2008-270736号公報の段落番号〔0171〕に記載の事項を本発明に適用することができる。
本発明の有機電界発光素子は、陽極と陰極との間に直流(必要に応じて交流成分を含んでもよい)電圧(通常2ボルト~15ボルト)、又は直流電流を印加することにより、発光を得ることができる。
本発明の有機電界発光素子の駆動方法については、特開平2-148687号、同6-301355号、同5-29080号、同7-134558号、同8-234685号、同8-241047号の各公報、特許第2784615号、米国特許5828429号、同6023308号の各明細書等に記載の駆動方法を適用することができる。
本発明の有機電界発光素子は、その発光波長は前記本発明の有機電界発光素子用材料の極大発光波長と同様であり、光の三原色のうち、青色の発光に用いる。本発明の有機電界発光素子では、前記一般式(1)で表される化合物を発光材料として用いて青色発光させる。
本発明の有機電界発光素子は、表示素子、ディスプレイ、バックライト、電子写真、照明光源、記録光源、露光光源、読み取り光源、標識、看板、インテリア、又は光通信等に好適に利用できる。特に、発光装置、照明装置、表示装置等の発光輝度が高い領域で駆動されるデバイスに好ましく用いられる。
本発明の発光装置は、本発明の有機電界発光素子を含むことを特徴とする。
次に、図2を参照して本発明の発光装置について説明する。
本発明の発光装置は、前記有機電界発光素子を用いてなる。
図2は、本発明の発光装置の一例を概略的に示した断面図である。図2の発光装置20は、透明基板(支持基板)2、有機電界発光素子10、封止容器16等により構成されている。
ここで、接着層14としては、エポキシ樹脂等の光硬化型接着剤や熱硬化型接着剤を用いることができ、例えば熱硬化性の接着シートを用いることもできる。
本発明の照明装置は、本発明の有機電界発光素子を含むことを特徴とする。
次に、図3を参照して本発明の照明装置について説明する。
図3は、本発明の照明装置の一例を概略的に示した断面図である。本発明の照明装置40は、図3に示すように、前述した有機EL素子10と、光散乱部材30とを備えている。より具体的には、照明装置40は、有機EL素子10の基板2と光散乱部材30とが接触するように構成されている。
光散乱部材30は、光を散乱できるものであれば特に制限されないが、図3においては、透明基板31に微粒子32が分散した部材とされている。透明基板31としては、例えば、ガラス基板を好適に挙げることができる。微粒子32としては、透明樹脂微粒子を好適に挙げることができる。ガラス基板及び透明樹脂微粒子としては、いずれも、公知のものを使用できる。このような照明装置40は、有機電界発光素子10からの発光が散乱部材30の光入射面30Aに入射されると、入射光を光散乱部材30により散乱させ、散乱光を光出射面30Bから照明光として出射するものである。
本発明の表示装置は、本発明の有機電界発光素子を含むことを特徴とする。
本発明の表示装置としては、例えば、テレビ、パーソナルコンピュータ、携帯電話、電子ペーパ等の表示装置とすることなどを挙げることができる。
実施例で用いた一般式(1)で表される化合物である発光材料1、7、8ならびに11~17の構造式、および、比較例で用いた発光材料Ref-1、Ref-2、Ref-11ならびにRef-12の構造式を以下にまとめて示す。
一般式(1)で表される化合物は、本明細書中に記載の方法や、その他公知の反応を組み合わせて合成することができる。以下に一般式(1)で表される化合物の具体的合成手順の代表例を記載する。
(合成例1)化合物1の合成
500mLの3つ口フラスコに、化合物1-a(60.0g、187mmol),ジフェニルアミン(38.06g、225mmol)、ヨウ化銅(18mmol、3.5g)、銅(37mmol、2.4g)、炭酸カリウム(374mmol、51.7g)とジフェニルエーテル180mLを入れ、窒素気流下200℃で14時間加熱した。反応溶液をセライトでろ過し、溶媒を留去した後にシリカゲルカラム(溶離液ヘキサン)にて精製を行った。溶媒留去後、得られた粗粉末をヘキサンで洗浄することにより化合物1-b(収量57.0g、収率84.3%)を白色粉末として得た。
[化合物1-cの合成]
2Lの3つ口フラスコに、窒素下にて化合物1-b(57.0g、158mmol)とジクロロメタン400mLを加え、氷浴下で攪拌しながら三臭化ホウ素のジクロロメタン溶液(濃度1mol/L、205mL、205mmol)を30分かけて滴下した。その後、反応液を室温下1時間攪拌した。反応溶液を氷水にあけた後、酢酸エチルで抽出した有機層を亜硫酸ナトリウム水溶液にて洗浄した。有機層の溶媒を減圧留去したのち、シリカゲルカラム(溶離液ヘキサン:酢酸エチル=9:1)にて精製を行った。溶媒留去後、ヘキサンで洗浄することにより化合物1-c(収量38.5g、収率73.1%)を白色固体として得た。
[化合物1-dの合成]
1Lの3つ口フラスコに、窒素気流下にて化合物1-d(38.5g、115mmol)とピリジン200mLを加え、氷浴下で攪拌しながらトリフルオロメタンスルホン酸無水物(23.6mL、140mmol)を30分かけて滴下した。その後、室温に昇温して6時間攪拌した。反応溶液に、氷浴下で水700mLを加え、得られた個体をろ別し水で洗浄したところ、化合物1-d(52.6g、~100%)を得た。
[化合物1-fの合成]
化合物1-e(9.0g、24.6mmol)、ビスピナコールジボラン(13.7g、54.1mmol)、酢酸カリウム(7.2g、73.8mmol)、(ジフェニルホスフィノフェロセン)パラジウムジクロリド(1.0g、1.2mmol)およびトルエン90mLを窒素気流下にて80℃で13時間加熱攪拌し、反応溶液を酢酸エチルで抽出する。溶媒を留去した後セライトろ過、次いでシリカゲルろ過を行い、溶媒を留去した後にエタノールを加えて得られた白色固体をろ別することで、化合物1-fを得た。
[化合物1-gの合成]
化合物1-f(6.75g、14.7mmol)、化合物1-d(8.2g、17.6mmol)、炭酸カリウム(4.8g、35.2mmol)、テトラキス(トリフェニルホスフィン)パラジウム(1.0g、0.9mmol)およびジメトキシエタン200mL、エタノール170mLを1Lの3つ口フラスコにて窒素気流下110℃で加熱し、得られた反応溶液の溶媒を留去、シリカゲルカラム(溶離液ヘキサン:酢酸エチル=9:1)で精製を行うことにより、化合物1-gを得た。
[化合物1-hの合成]
200mLの2つ口フラスコに化合物1-g(1.73g、2.7mmol)、N-p-ブロモフェニル-ジフェニルアミン(1.0g、3.2mmol)、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル(0.16g、0.38mmol)、リン酸三カリウム(3.4g、1.6mmol)、トリス(ジベンジリデンアセトン)ジパラジウム(88mg、0.1mmol)およびトルエン20mL、水10mLを加え、窒素気流下100℃で3時間加熱する。反応溶液を放冷後、トルエンにて有機層を抽出し、有機層を塩化ナトリウム水溶液にて洗浄し、溶媒留去後得られた残渣をシリカゲルカラム(溶離液ヘキサン:酢酸エチル=9:1)で精製を行うことにより、化合物1-hを得た。
[化合物1-iの合成]
100mLナスフラスコに化合物1-h(2.4g、3.1mmol)、およびTHF24mLを加えて氷浴下で溶解し、窒素気流下、メチルマグネシウムヨージド(12.5mmol)を滴下する。滴下後、反応溶液を室温まで昇温し、次いで80℃まで加熱して3時間加熱する。反応溶液を1M塩化アンモニウム水溶液にて中和した後、酢酸エチルにて有機層を抽出する。有機層を塩化ナトリウム水溶液で洗浄し、溶媒を留去した後の残渣をシリカゲルカラム(溶離液ヘキサン:酢酸エチル=9:1)で精製を行うことにより、化合物1-iを得た。
[化合物1の合成]
200mLの3つ口フラスコに化合物1-i(1.8g、2.4mmol)およびジクロロメタン60mLを加え、反応溶液を-75℃まで冷却する。その後に、メタンスルホン酸(46mg、0.48mmol)を滴下し、その後室温まで昇温する。反応溶液を水にあけ、酢酸エチルで抽出、溶媒留去後得られた残渣のカラム精製を行うことにより、化合物1を得た。
化合物1のNMRチャートを図5に示す。また、図5のNMRチャートの一部を拡大したものを図6に示す。
4,10-ジブロモピレン(20.55g、57.09mmol)、4-(4-ターシャリーブチルフェニル)フェニルボロン酸(14.51g、57.09mmol)、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル(5.62g、0.14mmol)、リン酸三カリウム(60.59g、285mmol)、トリス(ジベンジリデンアセトン)ジパラジウム(2.61g、2.9mmol)およびトルエン600mL、水300mLを加え、窒素気流下100℃で3時間加熱する。反応溶液を放冷後、トルエンにて有機層を抽出し、有機層を塩化ナトリウム水溶液にて洗浄し、溶媒留去後得られた残渣をシリカゲルカラム(溶離液ヘキサン:酢酸エチル=9:1)で精製を行うことにより、化合物12-aを得る事ができる。
1L三口フラスコに化合物12-a(15.62g、31.91mmol)、N-(4-クロロ-3-ヒドロキシフェニル)アセトアミド(7.11g、38.30mmol)、ジピバロイルメタン(1.18g、6.38mmol)、炭酸セシウム(51.98g、160mmol)、塩化銅(I)(6.32g、63.82mmol)およびN-メチルピロリドン300mLを加え、窒素気流化130℃で9時間撹拌する。放冷した反応溶液中の無機塩をセライトによりろ過し、純水/トルエンにて分液する。溶媒留去後得られた残渣をシリカゲルカラム(溶離液ヘキサン:酢酸エチル=2:1)で精製を行うことにより、化合物12-bを得る事ができる。
200mL三口フラスコに化合物12-b(3.46g、5.83mmol)、炭酸カリウム(3.22g、23.33mmol)、トリシクロヘキシルホスフィン テトラフルオロボレート(1.72g、4.67mmol)、酢酸パラジウム(0.52g、2.33mmol)、ジメチルアセトアミド35mLを加え、窒素気流化130℃で2時間撹拌する。放冷した反応溶液を水に注ぎ析出した固体を濾過し、THF中で再結晶精製を繰り返すことにより化合物12-cを得ることができる。
200mL三口フラスコに化合物12-c(1.60g、2.87mmol)、水酸化カリウム(1.29g、22.95mmol)、テトラヒドロフラン300mL、エタノール50mLおよび純水5mLを加え、窒素気流化で10時間還流する。放冷した反応溶液を酢酸エチルにて抽出し、溶媒留去後得られた残渣をシリカゲルカラム(溶離液ヘキサン:酢酸エチル=9:1)で精製を行うことにより、化合物12-dを得る事ができる。
200mL三口フラスコに化合物12-d(1.40g、2.72mmol)、2-ヨードナフタレン(2.07g、8.15mmol)、ナトリウムターシャリーブトキシド(0.86g、8.96mmol)、トリスジベンジリデンアセトンジパラジウム(0.25g、0.27mmol)、トリターシャリーブチルホスフィン(55mg、0.27mmol)、およびキシレン55mLを加え、窒素気流化で4時間還流する。放冷した反応溶液をトルエンにて抽出し、溶媒留去後得られた残渣をシリカゲルカラム(溶離液ヘキサン:トルエン=1:1)で精製を行うことにより、化合物12を得る事ができる。化合物12のNMRチャート(in CDCl3)を図7に示す。
<純度確認>
有機電界発光素子の作製に用いた材料は全て昇華精製を行い、高速液体クロマトグラフィー(東ソーTSKgel ODS-100Z)により純度(254nmの吸収強度面積比)が99.9%以上であることを確認した。
厚み0.5mm、2.5cm角のITO膜を有するガラス基板(ジオマテック社製、表面抵抗10Ω/□)を洗浄容器に入れ、2-プロパノール中で超音波洗浄した後、30分間UV-オゾン処理を行った。この透明陽極(ITO膜)上に真空蒸着法にて以下の有機化合物層を順次蒸着した。
第1層:HAT-CN:膜厚10nm
第2層:NPD:膜厚30nm
第3層:H-1および表1中に記載の発光材料(質量比93:7):膜厚30nm
第4層:BAlq:膜厚30nm
HAT-CNは下記構造を表す。
この得られた積層体を、大気に触れさせることなく、窒素ガスで置換したグローブボックス内に入れ、ガラス製の封止缶及び紫外線硬化型の接着剤(XNR5516HV、長瀬チバ(株)製)を用いて封止し、本発明の有機電界発光素子1~6、および比較素子1および2を得た。これらの素子を発光させた結果、各素子とも発光材料に由来する発光が得られた。
得られた各有機電界発光素子について、以下の試験を行った。
(a)外部量子効率
KEITHLEY社製ソースメジャーユニット2400を用いて、直流電圧を各素子に印加して発光させ、その輝度を輝度計(BM-8、(株)トプコン社製)を用いて測定した。発光スペクトルと発光波長はスペクトルアナライザー(PMA-11、浜松ホトニクス(株)製)を用いて測定した。これらを元に輝度が1000cd/m2付近の外部量子効率(η)を輝度換算法により算出し、相対外部量子効率は、Ref-2を用いた有機電界発光素子の外部量子効率を1.0としたときの相対値で下記表1中に表わした。数字が大きいほど効率が良いことを示しているため、好ましい。
(b)色度
各有機電界発光素子を輝度が1000cd/m2となるように直流電圧を印加して発光させたときの発光スペクトルから色度(x、y)を求めた(CIE1931表色系)。最も青味に優れる(0.14、0.08)を基準点Oとし、各有機電界発光素子の色度と基準点Oとの距離をCIE色度座標面上で換算して、以下の基準で評価した。その結果を下記表1に示した。
○:0.02未満である。
△:0.02以上0.035未満であるもの。
×:0.035以上であるもの。
各有機電界発光素子を輝度が1000cd/m2になるように直流電圧を印加して発光させ続け、輝度が500cd/m2に低下したときの色度(x’、y’)を発光スペクトルから求めた。駆動劣化前後のy値の変化Δy(=|y’-Δy|)から、以下の3段階で駆動劣化後の色度変化を評価した。
○ Δy≦0.01
△ 0.01<Δy≦0.02
× 0.02<Δy
-発光層形成用塗布液の調製-
発光材料1(0.25質量%)、ホスト材料ADN(5質量%)に、トルエン(94.75質量%)を混合し、発光層形成用塗布液1を得た。
発光層形成用塗布液1において発光材料1を発光材料3,6に変更した以外は発光層形成用塗布液1と同様にして、発光層形成用塗布液2,3を調製した。
ADNは下記構造の9,10-(ジ-2-ナフチル)アントラセンを表す。
25mm×25mm×0.7mmのガラス基板上にITOを150nmの厚みで蒸着し製膜したものを透明支持基板とした。この透明支持基板をエッチング、洗浄した。
このITOガラス基板上に、下記構造式で表されるPTPDES-2(ケミプロ化成製、Tg=205℃)2質量部を電子工業用シクロヘキサノン(関東化学製)98質量部に溶解し、厚みが約40nmとなるようにスピンコート(2,000rpm、20秒間、)した後、120℃で30分間乾燥と160℃で10分間アニール処理することで、正孔注入層を成膜した。
次いで、発光層上に、電子輸送層として、下記構造式で表されるBAlq(ビス-(2-メチル-8-キノリノラト)-4-(フェニル-フェノラト)-アルミニウム(III))を、厚みが40nmとなるように真空蒸着法にて形成した。
電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を、厚みが1nmとなるように真空蒸着法にて形成した。更に金属アルミニウムを70nm蒸着し、陰極とした。
以上により作製した積層体を、アルゴンガスで置換したグロ-ブボックス内に入れ、ステンレス製の封止缶及び紫外線硬化型の接着剤(XNR5516HV、長瀬チバ(株)製)を用いて封止することで、有機電界発光素子2-1~2-3を作製した。
得られた有機電界発光素子2-1~2-3は、いずれも暗青色の発光であり、輝度変調時の色度変化が小さかった。
厚み0.5mm、2.5cm角のITO膜を有するガラス基板(ジオマテック社製、表面抵抗10Ω/□)を洗浄容器に入れ、2-プロパノール中で超音波洗浄した後、30分間UV-オゾン処理を行った。この透明陽極(ITO膜)上に真空蒸着法にて以下の有機化合物層を順次蒸着した。
なお、以下の実施例及び比較例における蒸着速度は、特に断りのない場合は0.1nm/秒である。蒸着速度は水晶振動子を用いて測定した。また、以下の各層厚みは水晶振動子を用いて測定した。
第1層:HAT-CN:膜厚10nm
第2層:HT-2:膜厚35nm
第3層:H-1及び表2中に記載の発光材料(質量比=93:7):膜厚30nm
第4層:ET-1:膜厚30nm
得られた積層体を、大気に触れさせることなく、窒素ガスで置換したグローブボックス内に入れ、ガラス製の封止缶及び紫外線硬化型の接着剤(XNR5516HV、長瀬チバ(株)製)を用いて封止し、発光部分が2mm×2mmの正方形である有機電界発光素子11~17、および比較用の有機電界発光素子Ref-11およびRef-12を得た。各素子とも発光材料に由来する発光が観測された。得られた各有機電界発光素子について、以下の試験を行った。
各有機電界発光素子を輝度が1000cd/m2となるように直流電圧を印加して発光させたときの発光スペクトルから色度(x、y)を求めた(CIE1931表色系)。最も青味に優れる(0.14、0.08)を基準点Oとし、各有機電界発光素子の色度と基準点Oとの距離をCIE色度座標面上で換算して、以下の基準で評価した。その結果を下記表2に示した。
○ 0.04≦y≦0.12
△ 0.03≦y<0.04、0.12<y≦0.20
× y<0.03、0.20<y
各有機電界発光素子を初期輝度が50cd/m2になるように直流電圧を印加したときの色度座標を点W、初期輝度が1000cd/m2になるように直流電圧を印加してしたときの色度座標を点Sとした時の色度を発光スペクトルから求めた。各有機電界発光素子の点Wと点Sの距離をCIE色度座標面上で換算して、以下の基準で評価した。その結果を下記表2に示した。
○ Δy≦0.01
△ 0.01<Δy≦0.02
× 0.02<Δy
層構成を以下に示すものに変えた以外は実施例11と同様にして有機電界発光素子を作製し、実施例11と同様の評価を行った。結果を表3に示す。
第1層:HT-1:膜厚50nm
第2層:HT-3:膜厚40nm
第3層:H-2及び表3中に記載の発光材料(質量比=95:5):膜厚25nm
第4層:ET-5:膜厚5nm
第5層:ET-3:膜厚20nm
層構成を以下に示すものに変えた以外は実施例11と同様にして有機電界発光素子を作製し、実施例11と同様の評価を行った。結果を表4に示す。
第1層:HAT-CN:膜厚10nm
第2層:HT-3:膜厚35nm
第3層:H-1及び表4中に記載の発光材料(質量比=95:5):膜厚30nm
第4層:ET-4:膜厚30nm
層構成を以下に示すものに変えた以外は実施例11と同様にして有機電界発光素子を作製し、実施例11と同様の評価を行った。結果を表5に示す。
第1層:HAT-CN:膜厚10nm
第2層:HT-1:膜厚35nm
第3層:H-3及び表5中に記載の発光材料(質量比=93:7):膜厚30nm
第4層:ET-4:膜厚30nm
層構成を以下に示すものに変えた以外は実施例11と同様にして有機電界発光素子を作製し、実施例11と同様の評価を行った。結果を表6に示す。
第1層:HT-1:膜厚10nm
第2層:HT-2:膜厚30nm
第3層:H-4及び表6中に記載の発光材料(質量比=93:7):膜厚30nm
第4層:ET-2:膜厚30nm
3・・・陽極
4・・・正孔注入層
5・・・正孔輸送層
6・・・発光層
7・・・正孔ブロック層
8・・・電子輸送層
9・・・陰極
10・・・有機電界発光素子
11・・・有機層
12・・・保護層
14・・・接着層
16・・・封止容器
20・・・発光装置
30・・・光散乱部材
31・・・透明基板
30A・・光入射面
30B・・光出射面
32・・・微粒子
40・・・照明装置
Claims (19)
- 基板と、
該基板上に配置され、陽極及び陰極を含む一対の電極と、
該電極間に設置された1または複数の有機層とを有し、
該有機層は発光層を含み、該発光層はホスト材料と、少なくとも1つの下記一般式(1)で表される発光材料とを含むことを特徴とする有機電界発光素子。
- 前記一般式(1)において、Ra、Rb、RdおよびReがそれぞれ独立にアルキル基、アリール基およびヘテロアリール基のいずれかを表すことを特徴とする請求項1に記載の有機電界発光素子。
- 前記一般式(1)において、Rcが置換基を表すことを特徴とする請求項1または2に記載の有機電界発光素子。
- 前記一般式(1)において、XがCRa'Rb'(Ra'、Rb'はそれぞれ独立にアルキル基、アリール基、ヘテロアリール基のいずれかを表し、Ra'とRb'は共同して5または6員環を形成していてもよい。)またはNRc'(Rc'は置換基を表す。)を表すことを特徴とする請求項1~3のいずれか一項に記載の有機電界発光素子。
- 前記一般式(1)において、R1が少なくとも1つのN,N-ジアリールアミノ基、または、N,N-ジアリールアミノ基で置換されたアリール基を有することを特徴とする請求項1~4のいずれか一項に記載の有機電界発光素子。
- 前記一般式(1)で表される発光材料が、下記一般式(2)で表されることを特徴とする請求項1~5のいずれか一項に記載の有機電界発光素子。
- 前記一般式(1)で表される発光材料が、下記一般式(3)で表されることを特徴とする請求項1~5のいずれか一項に記載の有機電界発光素子。
XはCRaRb(Ra、Rbはそれぞれ独立に水素原子または置換基を表し、RaとRbは共同して5または6員環を形成していてもよい。)、NRc(Rcは水素原子または置換基を表す。)、O、S、SiRdRe(Rd、Reはそれぞれ独立に水素原子または置換基を表し、RdとReは共同して5または6員環を形成していてもよい。)のいずれかを表す。
R8~R11はそれぞれ独立に水素原子または置換基を表し、隣り合う2つのR8~R11は共同して飽和または不飽和の環を形成していてもよいが、2つ以上のR8~R11が共同して形成する環は2つ以下である。) - 前記一般式(1)で表される発光材料が、下記一般式(4)で表されることを特徴とする請求項1~5のいずれか一項に記載の有機電界発光素子。
R8~R11はそれぞれ独立に水素原子または置換基を表し、隣り合う2つのR8~R11は共同して飽和または不飽和の環を形成していてもよいが、2つ以上のR8~R11が共同して形成する環は2つ以下である。
R12、R13はそれぞれ独立に水素原子または置換基を表し、R12とR13は共同して5または6員環を形成していてもよい。) - 前記一般式(4)において、R2~R11のうち少なくとも1つが置換基を表すことを特徴とする請求項8に記載の有機電界発光素子。
- 前記一般式(4)において、R5およびR10のうち少なくとも1つが置換基を表すことを特徴とする請求項8に記載の有機電界発光素子。
- 前記一般式(1)で表される化合物の分子量が800以下であることを特徴とする請求項1~10のいずれか一項に記載の有機電界発光素子。
- 前記発光層に含まれる前記ホスト材料が、炭素数10~50の炭化水素縮合環構造を有することを特徴とする請求項1~11のいずれか一項に記載の有機電界発光素子。
- 前記ホスト材料の前記炭素数10~50の炭化水素縮合環構造がアントラセン骨格であることを特徴とする請求項12に記載の有機電界発光素子。
- 前記発光層が真空蒸着プロセスにて形成されたことを特徴とする請求項1~13のいずれか一項に記載の有機電界発光素子。
- 前記発光層が湿式プロセスにて形成されたことを特徴とする請求項1~13のいずれか一項に記載の有機電界発光素子。
- 請求項1~15のいずれか一項に記載の有機電界発光素子を用いた発光装置。
- 請求項1~15のいずれか一項に記載の有機電界発光素子を用いた表示装置。
- 請求項1~15のいずれか一項に記載の有機電界発光素子を用いた照明装置
- 下記一般式(1)で表される有機電界発光素子用の発光材料。
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