WO2013027693A1 - 有機電界発光素子、化合物、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、化合物、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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- WO2013027693A1 WO2013027693A1 PCT/JP2012/070976 JP2012070976W WO2013027693A1 WO 2013027693 A1 WO2013027693 A1 WO 2013027693A1 JP 2012070976 W JP2012070976 W JP 2012070976W WO 2013027693 A1 WO2013027693 A1 WO 2013027693A1
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Definitions
- the present invention relates to an organic electroluminescent element and a compound (material for organic electroluminescent element) used therein.
- the present invention also relates to a light emitting device, a display device or a lighting device using the organic electroluminescent element.
- An organic electroluminescent element (hereinafter also referred to as “element” or “organic EL element”) has an organic layer between a pair of electrodes, and an electron injected from a cathode and a hole injected from an anode are organic layers.
- Organic electroluminescence devices can emit light with high luminance at a low voltage, have a fast response speed, are thin and light, and are expected to be applied to a wide range of applications, and are actively researched and developed.
- an aromatic condensed hydrocarbon ring having 10 to 30 carbon atoms or an aromatic condensed heterocyclic ring having 8 to 30 carbon atoms is used as a core skeleton, and an aromatic group is used as a substituent.
- an aromatic group is used as a substituent.
- Patent Document 1 describes that a material in which a ring is formed by a single bond and a methylene chain with respect to a condensed ring structure such as pyrene can be used as a light-emitting material or a host material of an organic electroluminescence device. ing.
- Patent Document 2 discloses organic electroluminescence in which a compound having an aromatic condensed hydrocarbon ring having 5 to 60 carbon atoms or an aromatic condensed heterocyclic ring having 2 to 60 carbon atoms is used as a core, and a phenyl group is 1 or 2 per core skeleton. It describes that it can be used as a light-emitting material of an element.
- the present invention aims to solve the above problems. That is, the problem to be solved by the present invention is to provide an organic electroluminescent device in which the generation of dark spots during driving is suppressed.
- the present inventors have intensively studied for the purpose of providing an organic electroluminescence device in which the generation of dark spots during driving is suppressed. As a result, the inventors have found that the above problems can be solved by using a compound having a specific structure, and have provided the present invention described below.
- a substrate a pair of electrodes disposed on the substrate and including an anode and a cathode, and at least one organic layer including a light emitting layer between the electrodes, and any one of the at least one organic layer
- An organic electroluminescent device containing at least one compound represented by the following general formula (I) in the layer.
- Formula (I) (In the general formula (I), Q represents an aromatic condensed hydrocarbon ring having 10 to 30 carbon atoms or an aromatic condensed heterocycle having 8 to 30 carbon atoms.
- Ar independently represents an arylene group having 6 to 30 carbon atoms.
- L is CR 12 R 13 , NR 14 , SiR 15 R 16 (R 12 , R 13 , R 14 , R 15 and R 16 independently represents a fluorine atom, an alkyl group, an aryl group or a heteroaryl group.), Preferably an O atom or an S atom.
- Q preferably represents any one of naphthalene, anthracene, phenanthrene, pyrene, chrysene, perylene, and triphenylene. .
- Ar in the general formula (I) preferably independently represents a substituted or unsubstituted phenylene group.
- Q in the general formula (I) preferably represents pyrene.
- the compound represented by the general formula (I) is a compound represented by the following general formula (II): It is preferable.
- Formula (II) (In the general formula (II), R 1 to R 10 represent a hydrogen atom or a substituent, and R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10, and R 10 and R 1 are each independently a group represented by the following general formula B Replaced.)
- Formula B (In General Formula B, L 2 represents CR 12 R 13 , NR 14 , SiR 15 R 16 (R 12 , R 13 , R 14 , R 15 and R 16 are each independently a fluorine atom, an alkyl group, an aryl group or hetero Represents an aryl group), represents an O atom or an
- the compound represented by the general formula (II) is preferably a compound represented by the following general formula (III).
- the compound represented by the general formula (II) is preferably a compound represented by the following general formula (IV).
- the compound represented by the general formula (II) is preferably a compound represented by the following general formula (V).
- the compound represented by the general formula (II) is preferably a compound represented by the following general formula (VI).
- R 61 , R 62 and R 63 May be the same or different, and R 61 s , R 62 s, or R 63 s may be bonded to each other to form a ring.
- the compound represented by the general formula (I) is preferably contained in the light emitting layer.
- the compound represented by the general formula (I) is a light emitting material contained in the light emitting layer. preferable.
- the organic electroluminescent element according to [12] preferably further contains a host material in the light emitting layer.
- the host material preferably has an anthracene skeleton.
- the organic electroluminescence device of the present invention has an advantageous effect that generation of dark spots during driving is suppressed. Moreover, if the compound of this invention is used, such an outstanding organic electroluminescent element can be manufactured easily. Furthermore, the light emitting device, the display device, and the lighting device of the present invention have an advantageous effect that there are few dark spots.
- 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 compound represented by the general formula (I) of the present invention can be preferably used as a material for an organic electroluminescence device.
- the organic electroluminescent element of the present invention described later is characterized in that an organic layer constituting the organic electroluminescent element contains a compound represented by the general formula (I).
- Formula (I) (In the general formula (I), Q represents an aromatic condensed hydrocarbon ring having 10 to 30 carbon atoms or an aromatic condensed heterocycle having 8 to 30 carbon atoms.
- Ar independently represents an arylene group having 6 to 30 carbon atoms. Or a heteroarylene group having 3 to 30 carbon atoms, each L independently represents a divalent linking group, and n represents an integer of 3 to 5.)
- n 3 to 5 and 3 to 5 condensed ring structures of —Ar—L— are included per core skeleton.
- a compound having such a structure has not been conventionally known.
- the compound represented by the general formula (I) is used as a material for an organic electroluminescence device, generation of dark spots during driving is suppressed. It has not been known at all that the compound having the structure represented by the general formula (I) has such an effect, and an organic electroluminescent device having such an effect is advantageous when mounted on a display. It becomes.
- the compound of the present invention can provide an organic electroluminescent device exhibiting the above performance even when an organic electroluminescent device is produced at a high dew point temperature (for example, ⁇ 20 ° C.).
- the dew point temperature refers to “a temperature at which condensation starts when air containing water vapor is cooled”.
- the compound of the present invention can provide an organic electroluminescent device exhibiting the above performance even when an organic electroluminescent device is produced at a dew point temperature of ⁇ 20 ° C. or lower. Can be manufactured.
- the reason why the compound of the present invention can be preferably used for device production even in a range where the dew point temperature is high is that the logical reason why the structure of the compound of the present invention is advantageous for film formation in an atmosphere with a lot of moisture Is unknown and unpredictable.
- the dew point temperature in this specification was measured with a dew point meter (NS-100D, manufactured by Nippon Yakin Kagaku Kogyo Co., Ltd.) that detects moisture by a capacitance method.
- the hydrogen atom in the description of the general formula (I) 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.
- Q represents an aromatic condensed hydrocarbon ring having 10 to 30 carbon atoms or an aromatic condensed heterocycle having 8 to 30 carbon atoms.
- Q is preferably a condensed aromatic ring structure having three or more constituent rings. Moreover, it is more preferable that each constituent ring is a hydrocarbon ring.
- the condensed aromatic ring structure having three or more constituent rings is not particularly limited, but Q is preferably naphthalene, anthracene, phenanthrene, pyrene, chrysene, perylene, or triphenylene, and is preferably pyrene. More preferred.
- Q may have a substituent other than Ar and L. The substituent is not particularly limited, but preferably does not newly form a condensed ring with Q.
- Ar independently represents an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 3 to 30 carbon atoms. Ar may further have a substituent. Ar is more preferably an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 3 to 30 carbon atoms, particularly preferably an arylene group having 6 to 30 carbon atoms, each independently substituted or unsubstituted. It is particularly preferred to represent a substituted phenylene group.
- n represents an integer of 3 to 5, preferably 3 or 4, and particularly preferably 3.
- each L independently represents a divalent linking group.
- the linking group represented by L is not particularly limited, but in the present invention, L is CR 12 R 13 , NR 14 , SiR 15 R 16 (R 12 , R 13 , R 14 , R 15 and R 16 are each independently Represents a substituent, and preferably represents a fluorine atom, an alkyl group, an aryl group or a heteroaryl group.), Preferably an O atom or an S atom, and preferably a CR 12 R 13 , NR 14 or S atom. More particularly preferred.
- R 12 , R 13 , R 15 and R 16 substituted on carbon atoms and substituents on silicon atoms
- substituent group A include the following 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 preferably 2 to 20
- carbon atoms 0, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, anthranyl, etc.), amino groups (preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms).
- 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.
- Xy 1-naphthyloxy, 2-naphthyloxy, etc.
- a heterocyclic oxy group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms.
- pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc. 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, such as 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, such as 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.
- the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.
- the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.
- R 12 , R 13 , R 15 and R 16 each independently represent a fluorine atom, an alkyl group, an aryl group or a heteroaryl group.
- R 12 , R 13 , R 15 and R 16 are each independently a fluorine atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 14 carbon atoms; And more preferably a heteroaryl group containing at least one of N, O and S as a hetero atom, and is a straight-chain or branched alkyl group having 1 to 6 carbon atoms Is particularly preferred.
- R 12 and R 13 are preferably the same substituent.
- R 15 and R 16 are preferably the same substituent.
- R 12 , R 13 , R 15 and R 16 may jointly 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.
- R 14 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 propargyl
- hetero atom 0, particularly preferably 6 to 12 carbon atoms, including, for example, phenyl, p-methylphenyl, naphthyl, anthranyl, etc.), cyano group, heterocyclic group (including aromatic heterocyclic group, preferably carbon
- the hetero atom is, for example, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, a selenium atom, or a tellurium atom, specifically, pyridyl.
- the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.
- the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.
- R 14 is preferably an alkyl group, a perfluoroalkyl group, or an aryl group.
- 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 14 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 14 may further have a substituent, and the substituent is not particularly limited, but is preferably an alkyl group or an aryl group.
- the alkyl group at this time an unsubstituted linear alkyl group, an unsubstituted branched alkyl group, an unsubstituted cycloalkyl group and a perfluoroalkyl group are preferable, and a linear alkyl group having 1 to 6 carbon atoms, A branched alkyl group having 1 to 6 and a perfluoroalkyl group having 1 to 6 carbon atoms are more preferable, and a methyl group, an ethyl group, an isopropyl group, a t-butyl group, a t-amyl group, a neopentyl group, and a trifluoromethyl group are particularly preferable.
- the aryl group is preferably an aryl group having 6 to 14 carbon atoms, more preferably an aryl group having 6 to 10 carbon atoms, and particularly preferably a phenyl group.
- the compound represented by the general formula (I) is preferably a compound represented by the following general formula (II).
- Formula (II) (In the general formula (II), R 1 to R 10 represent a hydrogen atom or a substituent, and R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10, and R 10 and R 1 are each independently a group represented by the following general formula B Replaced.)
- Formula B (In the general formula B, L 2 represents CR 12 R 13 , NR 14 , SiR 15 R 16 , O atom or S atom.
- R 21 independently represents a substituent.
- O represents 0 to 4.
- each R 21 may be the same or different, and R 21 may be bonded to each other to form a ring.
- R 1 to R 10 represent a hydrogen atom or a substituent
- R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , 3 of R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 and R 10 and R 1 are substituted with the group represented by Formula B .
- R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 6 and R 7 , R 8 and R 9 and R 10 and R 1 are preferable.
- R 1 to R 10 a portion of R 1 to R 10 that is not substituted with the general formula B is a hydrogen atom or a substituent, and the substituent group A is preferably exemplified as the substituent. Can do. Of the R 1 to R 10 , it is more preferable that all the sites not substituted with the general formula B are hydrogen atoms.
- R 1 and R 2 are more preferably substituted at a total of 3 positions of R 6 and R 8 .
- R 21 in the group represented by the general formula B independently represents a substituent, and examples of the substituent include the substituent group A described above.
- R 21 is preferably a substituent having any one of a fluorine atom, an alkyl group, a silyl group, an aryl group, an aryloxy group, a cyano group, and an amino group.
- Specific examples include a fluorine atom, an alkyl group, a perfluoroalkyl group, a trialkylsilyl group, a phenyl group, a phenoxy group, and a disubstituted amino group.
- R 21 represents an alkyl group, a silyl group, an aryl group, an aryloxy group, or a disubstituted amino group.
- an unsubstituted linear alkyl group, an unsubstituted branched alkyl group, an unsubstituted cycloalkyl group and a perfluoroalkyl group are preferable, and a linear alkyl group having 1 to 6 carbon atoms, carbon A branched alkyl group having 1 to 6 carbon atoms and a perfluoroalkyl group having 1 to 6 carbon atoms are more preferable.
- the silyl group represented by R 21 is preferably an alkylsilyl group.
- the substituted or unsubstituted aryl group represented by R 21 and the disubstituted amino group include an aryl group substituted with an N, N-diarylamino group or an alkyl group, or a substituent having an N, N-diarylamino group A group is preferred.
- o represents 0 to 4, and o is preferably 0 or 1, and more preferably 0.
- each R 21 may be the same or different.
- R 21 may be bonded to each other to form a ring, but it is preferable not to form a ring.
- the compound represented by the general formula (II) is preferably a compound represented by any one of the following general formulas (III) to (VI).
- general formulas (III) to (VI) will be described in order.
- the compound represented by the general formula (II) is preferably a compound represented by the following general formula (III).
- L 31 , L 32 , L 33 and L 34 each independently represent CR 12 R 13 , NR 14 , SiR 15 R 16 , O atom or S atom.
- the explanation and preferred range of L 31 , L 32 , L 33 and L 34 are the same as the explanation and preferred range of L in the general formula (I).
- R 31 , R 32 and R 33 each independently represent a substituent.
- R 31 , R 32 and R 33 are the same as the explanation and preferred range of R 21 in the general formula (II).
- p1, q1 and r1 each independently represents an integer of 0 to 4.
- R 31 , R 32 and R 33 may be the same or different and R 31 , R 32 or R 33 are bonded to each other to form a ring. May be.
- the explanation and preferred range of p1, q1 and r1 are the same as the explanation and preferred range of o in the general formula (II).
- the compound represented by the general formula (II) is preferably a compound represented by the following general formula (IV).
- R 41 , R 42 and R 43 are And they may be the same or different, and R 41 s , R 42 s, or R 43 s may be bonded to each other to form a ring.
- L 41 , L 42 , L 43 and L 44 each independently represent CR 12 R 13 , NR 14 , SiR 15 R 16 , O atom or S atom.
- the explanation and preferred range of L 41 , L 42 , L 43 and L 44 are the same as the explanation and preferred range of L in the general formula (I).
- R 41 , R 42 and R 43 each independently represent a substituent.
- R 41 , R 42 and R 43 are the same as the explanation and preferred range of R 21 in the general formula (II).
- p2, q2 and r2 each independently represents an integer of 0 to 4.
- R 41 , R 42 and R 43 may be the same or different, and R 41 , R 42 or R 43 are bonded to each other to form a ring. May be.
- the explanation and preferred range of p2, q2 and r2 are the same as the explanation and preferred range of o in the general formula (II).
- the compound represented by the general formula (II) is preferably a compound represented by the following general formula (V).
- L 51 , L 52 , L 53 and L 54 each independently represent CR 12 R 13 , NR 14 , SiR 15 R 16 , O atom or S atom.
- the explanation and preferred range of L 51 , L 52 , L 53 and L 54 are the same as the explanation and preferred range of L in the general formula (I).
- R 51 , R 52 and R 53 each independently represent a substituent.
- R 51 , R 52 and R 53 are the same as the explanation and preferred range of R 21 in the general formula (II).
- p3, q3 and r3 each independently represents an integer of 0 to 4.
- R 51 , R 52 and R 53 may be the same or different, and R 51 , R 52 or R 53 are bonded to each other to form a ring. May be.
- the explanation and preferred range of p3, q3 and r3 are the same as the explanation and preferred range of o in the general formula (II).
- the compound represented by the general formula (II) is preferably a compound represented by the following general formula (VI).
- R 61 , R 62 and R 63 May be the same or different, and R 61 s , R 62 s, or R 63 s may be bonded to each other to form a ring.
- L 61 , L 62 , L 63 and L 64 each independently represent CR 12 R 13 , NR 14 , SiR 15 R 16 , O atom or S atom.
- the explanation and preferred range of L 61 , L 62 , L 63 and L 64 are the same as the explanation and preferred range of L in the general formula (I).
- R 61 , R 62 and R 63 each independently represent a substituent.
- R 61 , R 62 and R 63 are the same as the explanation and preferred range of R 21 in the general formula (II).
- p4, q4 and r4 each independently represents an integer of 0 to 4.
- R 61 , R 62 and R 63 may be the same or different, and R 61 , R 62 or R 63 are bonded to each other to form a ring. May be.
- the explanation and preferred range of p4, q4 and r4 are the same as the explanation and preferred range of o in the general formula (II).
- the compound represented by the general formula (II) is more preferably a compound represented by the general formula (III), the general formula (IV) or the general formula (VI).
- the compound represented by the general formula (I) preferably has a molecular weight of 1000 or less, more preferably 900 or less, particularly preferably 850 or less, and further preferably 800 or less.
- 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 sublimation temperature should not be too high from the viewpoint of vapor deposition suitability.
- the sublimation temperature of the compound represented by the general formula (I) (meaning a 10 mass% reduction temperature in the present specification) is preferably 300 ° C., more preferably 285 ° C. or less, and further preferably 270. It is below °C.
- the compound represented by the general formula (I) can be synthesized by combining the method described in US2008 / 0100208 and other known reactions. Further, for example, it can be synthesized by the following scheme.
- 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 at least one organic layer including a light emitting layer disposed between the electrodes, Any one of the at least one organic layer contains at least one compound represented by the general formula (I).
- 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 of the organic electroluminescent element, the substrate, the cathode and the anode are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described therein 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 has 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 at least one organic layer including a light emitting layer disposed between the electrodes, and at least one of the previous organic layers contains the compound represented by the general formula (I). It is characterized by that.
- at least one organic layer containing the compound represented by the general formula (1) is the light emitting layer.
- 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 (I) is contained in at least one of the organic layers disposed between the electrodes of the organic electroluminescent element, and is contained in the light emitting layer in the organic layer disposed between the electrodes. It is preferable to contain. However, the compound represented by the general formula (I) 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.
- Examples of the organic layer other than the light emitting layer that may contain the compound represented by the general formula (I) include a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge Examples thereof include a block layer (a hole block layer, an electron block layer, etc.), preferably an exciton block layer, a charge block layer, an electron transport layer, or an electron injection layer, more preferably an exciton. Block layer, charge blocking layer, or electron transport layer.
- the compound represented by the general formula (I) when the compound represented by the general formula (I) is contained in the light emitting layer, the compound represented by the general formula (I) 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 (I) is contained in an organic layer other than the light emitting layer, the compound represented by the general formula (I) 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.
- the organic layer disposed between the pair of electrodes is formed by a vacuum deposition process or a wet process of a composition containing at least one compound represented by the general formula (I).
- the light emitting layer is formed by a vacuum deposition process or a wet process, and the light emitting layer is formed by vapor deposition of a composition containing the compound represented by the general formula (1). It is particularly preferable.
- 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 the compound represented by the general formula (I), and the compound represented by the general formula (I) 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 (I) may be used as a host material of the light emitting layer.
- the compound represented by the general formula (I) is preferably used as a light emitting material, but even in that case, it is different from the compound represented by the general formula (I). These light emitting materials can be used in combination.
- the organic electroluminescent element of the present invention when the compound represented by the general formula (I) is used as a host material of the light emitting layer, or when used in an organic layer other than the light emitting layer, the general formula ( A light emitting material different from the compound represented by I) is used for the light emitting layer.
- the light emitting material that can be used in the present invention may be any of a phosphorescent light emitting material, a fluorescent light emitting material, and the like.
- 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 and the phosphorescent light-emitting material that can be used in the organic electroluminescent element of the present invention include, for example, paragraphs [0100] to [0164] of JP-A-2008-270736 and JP-A-2007-266458. Paragraph numbers [0088] to [0090] are described in detail, and the matters described in these publications can be applied to the present invention.
- Examples of phosphorescent materials that can be used in the present invention include US Pat. No. 6,303,238, US Pat. No. 6,097,147, WO 00/57676, WO 00/70655, WO 01/08230, WO 01/39234.
- more preferable light-emitting materials include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd complex, Examples thereof include phosphorescent metal complex compounds such as Dy complexes and Ce complexes.
- an Ir complex, a Pt complex, or a Re complex among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or Re complexes are preferred.
- an Ir complex and a Pt complex are particularly preferable, and an Ir complex is most preferable.
- 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 of only 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. It means that it is preferably 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 in addition to the compound represented by the general formula (I). 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,
- 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.
- a condensed aromatic hydrocarbon compound a naphthalene compound, an anthracene compound, a phenanthrene compound, a triphenylene compound, and a pyrene compound are preferable, an anthracene compound and a pyrene compound are more preferable, and an anthracene compound is 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 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 lowest excitation energy in the film state of the host material (S 1 energy), it is the color purity higher S 1 energy than that of the light emitting material, light emission efficiency, in view of 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 compound represented by the general formula (I) 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, a substituted group.
- R S1 , R S2 , and R S3 each independently represent a hydrogen atom
- Aryloxy group, substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, hydroxy group, cyano group, or substituted or unsubstituted amino group The table .
- Adjacent R S1, R S2, R S3 each other may be bonded to each other to form a saturated or unsaturated carbon ring .
- Ar S1 may be formed
- Ar S2 each independently a substituted or unsubstituted carbon atoms Represents an aryl group having 6 to 30 or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.)
- 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, or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms.
- 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.
- a group or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms Y S1 and Y S2 are each independently a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, or a substituted or unsubstituted group; Represents a substituted arylene group having 6 to 30 carbon atoms, and n and m each independently represents an integer of 0 to 5.
- 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 carbocyclic ring or an unsaturated carbocyclic ring.
- 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, or 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 are each independently 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 and 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 6 carbon atoms.
- Adjacent R S11 and R S12 may be bonded to each other to form a saturated carbocyclic ring or an unsaturated carbocyclic ring.
- 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 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 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 Q Sa each independently represents a hydrogen atom, a cyano 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 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, an aryloxy group having 6 to 30 carbon atoms, a substituted group Alternatively, it represents 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 atom and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, more preferably a hydrogen atom.
- 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 each independently represent 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 a Represents a reeloxy group, a substituted
- 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.
- 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 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 the layer on the anode side adjacent to the light emitting layer, and it is particularly preferable that the hole transport material be contained in the hole transport layer.
- 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 with respect to 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 compounds such as TCNQ
- F 4 -TCNQ tetracyanoquinodimethane
- hexaazatriphenylene compounds such as hexacyanohexaazatriphenylene (HAT-CN)
- molybdenum oxide molybdenum oxide.
- 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.
- Materials used for the electron blocking layer is a color purity higher S 1 energy than that of the light emitting material, light emission efficiency, in view of 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 (I) 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 still 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 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 (I) 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 (I) 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, and even 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.
- Materials used in the hole blocking layer is a color purity higher S 1 energy than that of the light emitting material, light emission efficiency, in view of 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 (I), a compound represented by the following general formula (O-1), and a compound represented by the following general formula (P) A compound can be mentioned.
- the compound represented by the general formula (O-1) and the compound represented by the general formula (P) 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, and 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.
- an alkyl group, an aryl group or a cyano group can be mentioned, an alkyl group or an aryl group is more preferable, and an aryl group is still more preferable.
- 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, and 0 or 1 is more preferably 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 , more preferably A O1 is a nitrogen atom, A O2 to A O4 are C—R A , and R A is all a hydrogen atom.
- R A represents a hydrogen atom, an alkyl group (preferably having a carbon number of 1 to 8), an aryl group (preferably having a carbon number of 6 to 30), or a heteroaryl group (preferably having a carbon number of 4 to 12). It may have a substituent selected from the substituent group A.
- the plurality of RA may be the same or different.
- R A is preferably a hydrogen atom or an alkyl group, and 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 from the viewpoint of device efficiency, and most preferably 2 from the viewpoint 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 130 ° 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 layer on the cathode side adjacent to the light emitting layer. 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). represents, they may .nP have a substituent selected from the above-described substituent group a denotes an integer of 1 to 10, if 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 1 to 8 carbon atoms) and an aryl group (preferably 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 Represents an integer of 0 to 4, and when there are a plurality of R P1 to R P3 and R ′′ P1 to R ′′ P3 , they may be the same or different.
- L P1 to L P3 each represents a single bond or an aryl ring Or represents a divalent linking group consisting of a heteroaryl ring, and * represents a bonding position with the anthracene ring of the general formula (P).
- R P (P-1) preferred substituents other than the substituent represented by ⁇ (P-3) is an aryl group, more preferably a phenyl group, a biphenyl group, a terphenyl group, or 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, and terphenyls. Or a naphthyl group, most preferably a phenyl group.
- L P1 to L P3 are each preferably a single bond or a divalent linking group consisting of 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 of the protective layer may be an inorganic material or an organic material.
- 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 electroluminescent element 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-5-29080, JP-A-7-134558, JP-A-8-234585, and JP-A-8-2441047.
- the driving methods described in each publication, Japanese Patent No. 2,784,615, 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 around 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 organic electroluminescence device of the present invention is not limited in its emission wavelength, but is preferably used for blue or white light emission. Among these, in the organic electroluminescent element of the present invention, it is preferable to emit light using the compound represented by the general formula (I) as a light emitting material, and it is particularly preferable to emit blue light.
- 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 (supporting 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.
- the materials other than F1 to F8 and D1 to D4 used for manufacturing the organic electroluminescent element are shown below.
- Example 2 Organic electroluminescent elements 1-1 to 1-8 of the present invention and comparative elements 1-1 to 1-4
- Purity of materials used All materials used for device fabrication were sublimated and purified by high performance liquid chromatography (Tosoh TSKgel ODS-100Z). confirmed.
- First layer HAT-CN: film thickness 10 nm
- Second layer NPD: film thickness 30 nm
- Third layer host material HO-1 and light emitting material described in Table 1 below (mass ratio 95: 5): film thickness 30 nm
- Fourth layer BAlq: film thickness 30 nm
- 1 nm of lithium fluoride and 100 nm of metal aluminum were vapor-deposited in this order, and it was set as the cathode.
- a patterned mask (a mask having a light emitting area of 2 mm ⁇ 2 mm) was placed on the lithium fluoride layer, and metal aluminum was evaporated.
- the obtained laminate is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.) are used.
- XNR5516HV ultraviolet curable adhesive
- the organic electroluminescent devices 1-1 to 1-8 and the comparative devices 1-1 to 1-4 of the present invention were obtained.
- A Number of dark spots after driving An organic electroluminescent element (prepared in an environment with a dew point temperature of ⁇ 20 ° C.) was set in an emission spectrum measurement system (ELS1500) manufactured by Shimadzu Corporation, and a constant current density (40 mA / A direct current voltage was applied at cm 2 ) and driven for 100 hours. By visually counting the number of dark spots after driving, the number of dark spots generated during driving was evaluated. The smaller the number of dark spots, the better.
- Example 3 (Production of Comparative Element 2-1) (1) Preparation of light emitting layer forming coating solution Methyl ethyl ketone (99.99% by mass) was mixed with the above light emitting material D1 (0.1% by mass) and the following host material HO-2 (0.9% by mass). A coating solution 1 for forming a light emitting layer for a comparative example was obtained.
- the light emitting layer forming coating solution 1 was 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
- the light emitting layer forming coating solutions 2 to 4 for Examples were used in the same manner as the light emitting layer forming coating solution 1 except that the light emitting material D1 in the light emitting layer forming coating solution 1 was changed to the light emitting material shown in Table 2 below.
- the devices 2-1, 2-2 and 2-3 of the present invention were produced in the same manner as the comparative device 2-1, except that the light emitting layer forming coating solution was changed as shown in Table 2.
- the electroluminescent device of the present invention using the compound represented by the general formula (I) as the luminescent material of the luminescent layer has a number of dark spots after driving as compared with each comparative device. I found that there were few.
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Abstract
Description
例えば、特許文献1には、ピレンなどの縮環構造に対して単結合とメチレン鎖などで環を形成した材料が、有機電界発光素子の発光材料やホスト材料などとして用いることができることが記載されている。この文献にはアリールピレンがメチレン鎖を介してピレン骨格と縮環した化合物がいくつか例示されているものの、ピレン骨格とアリール置換基との縮環がピレン骨格当たり1または2個の態様のみが記載されている。
特許文献2には、炭素数5~60の芳香族縮合炭化水素環または炭素数2~60の芳香族縮合ヘテロ環をコアとして、フェニル基がコア骨格当たり1または2個の化合物を有機電界発光素子の発光材料として用いることができることが記載されている。
本発明は上記問題を解決することを目的とするものである。すなわち、本発明が解決しようとする課題は、駆動中のダークスポットの発生が抑制された有機電界発光素子を提供することにある。
一般式(I)
[2] [1]に記載の有機電界発光素子は、前記一般式(I)において、LがCR12R13、NR14、SiR15R16(R12、R13、R14、R15およびR16はそれぞれ独立にフッ素原子、アルキル基、アリール基またはヘテロアリール基を表す。)、O原子またはS原子であることが好ましい。
[3] [1]または[2]に記載の有機電界発光素子は、前記一般式(I)において、Qがナフタレン、アントラセン、フェナントレン、ピレン、クリセン、ペリレンおよびトリフェニレンのいずれかを表すことが好ましい。
[4] [1]~[3]のいずれか一項に記載の有機電界発光素子は、前記一般式(I)において、Arがそれぞれ独立に置換または無置換のフェニレン基を表すことが好ましい。
[5] [1]~[4]のいずれか一項に記載の有機電界発光素子は、前記一般式(I)において、Qがピレンを表すことが好ましい。
[6] [1]~[5]のいずれか一項に記載の有機電界発光素子は、前記一般式(I)で表される化合物が、下記一般式(II)で表される化合物であることが好ましい。
一般式(II)
一般式B
[7] [6]に記載の有機電界発光素子は、前記一般式(II)で表される化合物が、下記一般式(III)で表される化合物であることが好ましい。
一般式(III)
[8] [6]に記載の有機電界発光素子は、前記一般式(II)で表される化合物が、下記一般式(IV)で表される化合物であることが好ましい。
一般式(IV)
[9] [6]に記載の有機電界発光素子は、前記一般式(II)で表される化合物が、下記一般式(V)で表される化合物であることが好ましい。
一般式(V)
[10] [6]に記載の有機電界発光素子は、前記一般式(II)で表される化合物が、下記一般式(VI)で表される化合物であることが好ましい。
一般式(VI)
[11] [1]~[10]のいずれか一項に記載の有機電界発光素子は、前記一般式(I)で表される化合物が前記発光層に含有されることが好ましい。
[12] [1]~[11]のいずれか一項に記載に有機電界発光素子は、前記一般式(I)で表される化合物が、前記発光層に含有される発光材料であることが好ましい。
[13] [12]に記載の有機電界発光素子は、前記発光層に、さらにホスト材料を含有することが好ましい。
[14] [13]に記載の有機電界発光素子は、前記ホスト材料がアントラセン骨格を有することが好ましい。
[15] [1]~[14]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。
[16] [1]~[14]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。
[17] [1]~[14]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。
[18] 下記一般式(III)で表される化合物。
一般式(III)
本発明の一般式(I)で表される化合物は、有機電界発光素子用材料として好ましく用いることができる。後述の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前記一般式(I)で表される化合物を含有することを特徴とする。
一般式(I)
また、本発明の化合物は、高い露点温度(例えば-20℃)で有機電界発光素子を製造するときにおいても、上記の性能を示す有機電界発光素子を得ることができる。ここで本明細書中、露点温度とは、「水蒸気を含む空気を冷却したとき、凝結が始まる温度」のことを言う。本発明の化合物は露点温度が-20℃以下の範囲で有機電界発光素子を製造するときにおいても、上記の性能を示す有機電界発光素子を得ることができ、幅広い露点温度で有機電界発光素子を製造することができる。本発明の化合物が、露点温度が高い範囲でも素子製造に好ましく用いることができることは、本発明の化合物の構造が水分の多い雰囲気下での成膜に有利となるような論理的な理由は現時点では不明であり、予測できないものであった。
本明細書中における露点温度は、静電容量方式により水分を検知するタイプの露点計(NS-100D、日本冶金化学工業社製)で測定した。
本発明において、前記一般式(I)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。
前記構成環が3環以上の縮合芳香環構造としては特に制限は無いが、前記Qがナフタレン、アントラセン、フェナントレン、ピレン、クリセン、ペリレンおよびトリフェニレンのいずれかであることが好ましく、ピレンであることがより好ましい。
前記QはAr、L以外の置換基を有していてもよい。該置換基としては特に制限はないが、新たに前記Qとの縮環を形成しないことが好ましい。
Arはさらに置換基を有していてもよい。
前記Arは、炭素数6~30のアリーレン基または炭素数3~30のヘテロアリーレン基を表すことがより好ましく、炭素数6~30のアリーレン基を表すことが特に好ましく、それぞれ独立に置換または無置換のフェニレン基を表すことがより特に好ましい。
《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。
前記R12、R13、R15およびR16はそれぞれ独立にフッ素原子、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3~20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より好ましく、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特に好ましい。また、合成容易性の観点からは、R12およびR13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R15およびR16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。
R14はさらに置換基を有していてもよく、該置換基としては特に制限はないが、アルキル基またはアリール基が好ましい。このときのアルキル基としては、無置換の直鎖アルキル基、無置換の分枝アルキル基、無置換のシクロアルキル基およびペルフルオロアルキル基が好ましく、炭素数1~6の直鎖アルキル基、炭素数1~6の分枝アルキル基および炭素数1~6のペルフルオロアルキル基がより好ましく、メチル基、エチル基、イソプロピル基、t-ブチル基、t-アミル基、ネオペンチル基およびトリフルオロメチル基が特に好ましく、メチル基、エチル基、イソプロピル基およびt-ブチル基がより特に好ましい。一方、このときのアリール基としては、炭素数6~14のアリール基が好ましく、炭素数6~10のアリール基がより好ましく、フェニル基が特に好ましい。
一般式(II)
一般式B
前記一般式(II)において、R1~R10のうち、一般式Bで置換されていない部位については、水素原子または置換基であり、該置換基としては前記置換基群Aを好ましく挙げることができる。前記R1~R10のうち、一般式Bで置換されていない部位は全て水素原子であることがより好ましい。
R21が表すアルキル基としては、無置換の直鎖アルキル基、無置換の分枝アルキル基、無置換のシクロアルキル基およびペルフルオロアルキル基が好ましく、炭素数1~6の直鎖アルキル基、炭素数1~6の分枝アルキル基および炭素数1~6のペルフルオロアルキル基がより好ましい。R21が表すシリル基としては、アルキルシリル基が好ましい。R21が表す置換または無置換のアリール基、および、ジ置換アミノ基としては、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好ましい。
oが2~4の場合、各R21は同一でも異なっていてもよい。R21同士が互いに結合して環を形成していてもよいが、環を形成しないことが好ましい。
一般式(III)
前記一般式(III)中、m1、n1は0または1であり、m1+n1=1である。この中でも、m1が0であり、かつ、n1が1であることが、駆動中のダークスポットの発生を抑制する観点から好ましい。
前記一般式(III)中、R31、R32およびR33はそれぞれ独立に置換基を表す。R31、R32およびR33の説明と好ましい範囲は、前記一般式(II)におけるR21の説明と好ましい範囲と同じである。
前記一般式(III)中、p1、q1およびr1はそれぞれ独立に0~4の整数を表す。p1、q1およびr1が2~4の場合、R31、R32およびR33は同一でも異なっていてもよく、R31同士、R32同士またはR33同士が互いに結合して環を形成していてもよい。p1、q1およびr1の説明と好ましい範囲は、前記一般式(II)におけるoの説明と好ましい範囲と同じである。
一般式(IV)
前記一般式(IV)中、m2、n2は0または1であり、m2+n2=1である。この中でも、m2が0であり、かつ、n2が1であることが、駆動中のダークスポットの発生を抑制する観点から好ましい。
前記一般式(IV)中、R41、R42およびR43はそれぞれ独立に置換基を表す。R41、R42およびR43の説明と好ましい範囲は、前記一般式(II)におけるR21の説明と好ましい範囲と同じである。
前記一般式(IV)中、p2、q2およびr2はそれぞれ独立に0~4の整数を表す。p2、q2およびr2が2~4の場合、R41、R42およびR43は同一でも異なっていてもよく、R41同士、R42同士またはR43同士が互いに結合して環を形成していてもよい。p2、q2およびr2の説明と好ましい範囲は、前記一般式(II)におけるoの説明と好ましい範囲と同じである。
一般式(V)
前記一般式(V)中、m3、n3は0または1であり、m3+n3=1である。この中でも、m3が1であり、かつ、n3が0であることが好ましい。
前記一般式(V)中、R51、R52およびR53はそれぞれ独立に置換基を表す。R51、R52およびR53の説明と好ましい範囲は、前記一般式(II)におけるR21の説明と好ましい範囲と同じである。
前記一般式(V)中、p3、q3およびr3はそれぞれ独立に0~4の整数を表す。p3、q3およびr3が2~4の場合、R51、R52およびR53は同一でも異なっていてもよく、R51同士、R52同士またはR53同士が互いに結合して環を形成していてもよい。p3、q3およびr3の説明と好ましい範囲は、前記一般式(II)におけるoの説明と好ましい範囲と同じである。
一般式(VI)
前記一般式(VI)中、m3、n3は0または1であり、m3+n3=1である。この中でも、m3が1であり、かつ、n3が0であることが好ましい。
前記一般式(VI)中、R61、R62およびR63はそれぞれ独立に置換基を表す。R61、R62およびR63の説明と好ましい範囲は、前記一般式(II)におけるR21の説明と好ましい範囲と同じである。
前記一般式(VI)中、p4、q4およびr4はそれぞれ独立に0~4の整数を表す。p4、q4およびr4が2~4の場合、R61、R62およびR63は同一でも異なっていてもよく、R61同士、R62同士またはR63同士が互いに結合して環を形成していてもよい。p4、q4およびr4の説明と好ましい範囲は、前記一般式(II)におけるo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、発光層を含む少なくとも一層の有機層とを有し、前記少なくとも一層の有機層のいずれかの層に、少なくとも一種の前記一般式(I)で表される化合物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、発光層を含む少なくとも一層の有機層を有し、前有機層のうち少なくとも一層に前記一般式(I)で表される化合物を含むことを特徴とする。本発明の有機電界発光素子は、前記一般式(1)で表される化合物を含む少なくとも一層の有機層が、前記発光層であることが好ましい。
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(I)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(I)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(I)で表される化合物を含む組成物の真空蒸着プロセスまたは湿式プロセスにより形成されていることが好ましく、前記発光層が真空蒸着プロセスまたは湿式プロセスにより形成されていることがより好ましく、発光層が前記一般式(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特に好ましい。
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(I)で表される化合物を発光材料とすることが好ましいが、その場合であっても前記一般式(I)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(I)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(I)で表される化合物とは別の発光材料を発光層に用いる。
本発明において用いることができる発光材料は、燐光発光材料、蛍光発光材料等のいずれであってもよい。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。
本発明に使用できる燐光発光材料としては、例えば、米国特許第6303238号明細書、米国特許第6097147号明細書、WO00/57676号公報、WO00/70655号公報、WO01/08230号公報、WO01/39234号公報、WO01/41512号公報、WO02/02714号公報、WO02/15645号公報、WO02/44189号公報、WO05/19373号公報、特開2001-247859号公報、特開2002-302671号公報、特開2002-117978号公報、特開2003-133074号公報、特開2002-235076号公報、特開2003-123982号公報、特開2002-170684号公報、欧州特許公開第1211257号公報、特開2002-226495号公報、特開2002-234894号公報、特開2001-247859号公報、特開2001-298470号公報、特開2002-173674号公報、特開2002-203678号公報、特開2002-203679号公報、特開2004-357791号公報、特開2006-256999号公報、特開2007-19462号公報、特開2007-84635号公報、特開2007-96259号公報等の特許文献に記載の燐光発光化合物などが挙げられ、中でも、更に好ましい発光材料としては、Ir錯体、Pt錯体、Cu錯体、Re錯体、W錯体、Rh錯体、Ru錯体、Pd錯体、Os錯体、Eu錯体、Tb錯体、Gd錯体、Dy錯体、及びCe錯体等の燐光発光性金属錯体化合物が挙げられる。特に好ましくは、Ir錯体、Pt錯体、又はRe錯体であり、中でも金属-炭素結合、金属-窒素結合、金属-酸素結合、金属-硫黄結合の少なくとも一つの配位様式を含むIr錯体、Pt錯体、又はRe錯体が好ましい。更に、発光効率、駆動耐久性、色度等の観点で、Ir錯体、Pt錯体が特に好ましく、Ir錯体が最も好ましい。
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。
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(I)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(I)で表される化合物を用いることができる。
前記一般式(I)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(I)で表される化合物、下記一般式(O-1)で表される化合物および下記一般式(P)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)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、その発光波長に制限はないが、青色または白色の発光に用いるのが好ましい。その中でも、本発明の有機電界発光素子では、前記一般式(I)で表される化合物を発光材料として用いて発光させることが好ましく、特に青色発光させることが好ましい。
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。
(合成)
前記一般式(I)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。以下に前記一般式(I)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F1の合成
以下のスキームにしたがって、化合物F1を合成した。
(本発明の有機電界発光素子1-1~1-8、および比較素子1-1~1-4)
(1)使用材料純度
素子作成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99.0%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、露点温度-20℃の環境下で、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:ホスト材料HO-1および下記表1に記載の発光材料(質量比95:5):膜厚30nm
第4層:BAlq:膜厚30nm
この上に、フッ化リチウム1nm及び金属アルミニウム100nmをこの順に蒸着し陰極とした。なお、フッ化リチウムの層上に、パターニングしたマスク(発光領域が2mm×2mmとなるマスク)を設置し、金属アルミニウムを蒸着した。
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1-1~1-8、および比較素子1-1~1-4を得た。
上記にて得られた本発明の有機電界発光素子1-1~1-8、および比較素子1-1~1-4について、以下の評価を行った。その結果を下記表1に記載する。
有機電界発光素子を(露点温度-20℃の環境下で作成)(株)島津製作所製の発光スペクトル測定システム(ELS1500)にセットし、一定電流密度(40mA/cm2)にて直流電圧を印加し、100時間駆動させた。駆動後のダークスポットの数を目視により数えることにより、駆動中に発生したダークスポットの多少を評価した。ダークスポット数は少ないほど好ましい。
(比較素子2-1の作製)
(1)発光層形成用塗布液の調製
上記発光材料D1(0.1質量%)、下記ホスト材料HO-2(0.9質量%)に、メチルエチルケトン(98.99質量%)を混合し、比較例用の発光層形成用塗布液1を得た。
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質量部をシクロヘキサノン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、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、比較素子2-1を作製した。
発光層形成用塗布液1において発光材料D1を下記表2に記載の発光材料に変更した以外は発光層形成用塗布液1と同様にして、実施例用の発光層形成用塗布液2~4を調製した。
また、発光層形成用塗布液を表2に示すように変更した以外は、比較素子2-1と同様にして本発明の素子2-1、2-2および2-3を作製した。
実施例2と同様に駆動後のダークスポット数の評価を行った。得られた結果を下記表2に示す。
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 (18)
- 前記一般式(I)において、LがCR12R13、NR14、SiR15R16(R12、R13、R14、R15およびR16はそれぞれ独立にフッ素原子、アルキル基、アリール基またはヘテロアリール基を表す。)、O原子またはS原子である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(I)において、Qがナフタレン、アントラセン、フェナントレン、ピレン、クリセン、ペリレンおよびトリフェニレンのいずれか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(I)において、Arがそれぞれ独立に置換または無置換のフェニレン基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(I)において、Qがピレンを表す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(I)で表される化合物が、下記一般式(II)で表される化合物であ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。
一般式(II)
一般式B
- 前記一般式(II)で表される化合物が、下記一般式(III)で表される化合物であることを特徴とする請求項6に記載の有機電界発光素子。
一般式(III)
- 前記一般式(II)で表される化合物が、下記一般式(IV)で表される化合物であることを特徴とする請求項6に記載の有機電界発光素子。
一般式(IV)
- 前記一般式(II)で表される化合物が、下記一般式(V)で表される化合物であることを特徴とする請求項6に記載の有機電界発光素子。
一般式(V)
- 前記一般式(II)で表される化合物が、下記一般式(VI)で表される化合物であることを特徴とする請求項6に記載の有機電界発光素子。
一般式(VI)
- 前記一般式(I)で表される化合物が前記発光層に含有され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。
- 前記一般式(I)で表される化合物が、前記発光層に含有される発光材料であることを特徴とする請求項1~11のいずれか一項に記載に有機電界発光素子。
- 前記発光層に、さらにホスト材料を含有す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。
- 前記ホスト材料がアントラセン骨格を有することを特徴とする請求項13に記載の有機電界発光素子。
- 請求項1~14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1~14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1~14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(III)で表される化合物。
一般式(III)
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