WO2007148660A1 - 複素環含有アリールアミン誘導体を用いた有機エレクトロルミネッセンス素子 - Google Patents
複素環含有アリールアミン誘導体を用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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Definitions
- the present invention relates to an organic electoluminescence device using a heterocyclic ring-containing arylamine derivative.
- An organic electroluminescence device (hereinafter, electroluminescence is abbreviated as EL) can apply an electric field to recombine energy of holes injected from an anode and electrons injected from a cathode. It is a self-luminous element that utilizes the principle that a fluorescent substance emits light.
- Non-Patent Document 1 Since the EL device report (Non-Patent Document 1 etc.) was made, research on organic EL devices using organic materials as constituent materials has been actively conducted.
- Tang et al. Use tris (8-hydroxyquinolinol aluminum) for the light-emitting layer and triphenyldiamin derivative for the hole transport layer.
- the advantages of the stacked structure are to increase the efficiency of hole injection into the light-emitting layer, to increase the efficiency of exciton generation by recombination by blocking electrons injected from the cathode, and to generate in the light-emitting layer For example, confinement of excitons.
- the device structure of an organic EL device includes a hole transport (injection) layer, a two-layer type of an electron transporting light emitting layer, or a hole transport (injection) layer, a light emitting layer, an electron transport ( The three-layer type isotropic of the injection layer is well known.
- the element structure and the formation method have been devised in order to increase the recombination efficiency between injected holes and electrons.
- Patent Documents 1 and 2 Conventionally, as a hole injection material used for an organic EL element, a material having a phenylenediamine structure represented by Patent Documents 1 and 2 has been known and widely used.
- the hole transport material arylene-based materials containing a benzidine skeleton described in Patent Documents 3 and 4 have been used.
- Patent Documents 5 to 7 disclose arylamine compounds containing strong rubazole. Further, when such a material is used as a hole transport material, it has a feature that the light emission efficiency is improved, but at the same time, there is a drawback that the driving voltage is significantly increased and the device life is extremely shortened.
- Patent Document 8 discloses a device using two or more hole injection transport layers in which an ionization potential ⁇ I is set in a stepped manner in order to efficiently inject holes from the anode to the light emitting layer.
- the material system described in Patent Document 8 has insufficient luminous efficiency and lifetime.
- Patent Document 1 JP-A-8-291115
- Patent Document 2 JP 2000-309566 Koyuki
- Patent Document 3 US Patent No. 5, 061, 569
- Patent Document 4 Japanese Patent Laid-Open No. 2001-273978
- Patent Document 5 US Patent 6, 242, 115 specification
- Patent Document 6 JP 2000-302756 A
- Patent Document 7 Japanese Patent Application Laid-Open No. 11 144873
- Patent Document 8 JP-A-6-314594
- Non-Patent Document 1 C. W. Tang, S. A. Vanslyke, Applied Physics Letters, 51, 913 (1987)
- An object of the present invention is to provide an organic EL device having a low voltage, high efficiency, and long life.
- the following organic EL device is provided.
- an anode and a cathode a light emitting layer composed of at least an organic compound between the anode and the cathode, and two or more layers in a hole injection and transport zone between the anode and the light emitting layer,
- the layer in contact with the light emitting layer in the hole injection 'transport zone described above contains a compound represented by the following formula (1), and the layer in the hole injection' transport zone has the anode and the light emitting layer.
- An organic electoluminescence device in which a layer located between layers in contact with the layer contains an amine derivative represented by the following formula (2).
- Z is a substituted or unsubstituted nitrogen-containing heterocyclic group, and is a linking group formed by bonding 1 to 4 divalent aromatic groups which may have a substituent.
- Ar and Ar are each
- L is a substituted or unsubstituted arylene group having 10 to 40 nuclear carbon atoms, Ar to Ar
- 2 3 is a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 60 nuclear carbon atoms, or
- Ar to Ar are substituted or unsubstituted aromatic carbon atoms having 6 to 60 nuclear carbon atoms, respectively.
- It is a hydrogen ring group or a substituted or unsubstituted aromatic heterocyclic group having 6 to 60 nuclear atoms, R is a substituent, and n represents an integer of 2 to 4.
- R and R are each a substituent, and are connected to each other to form a saturated or unsaturated ring.
- Ar to Ar are each a substituted or unsubstituted aromatic group having 6 to 60 nuclear carbon atoms.
- At least one of Ar to Ar in formula (4) is a substituted or unsubstituted biphenyl group 3
- R to R are each a substituent, and are connected to each other to form a saturated or unsaturated ring.
- Ar to Ar are substituted or unsubstituted 6 to 60 nuclear carbon atoms, respectively.
- At least one of Ar to Ar in formula (5) is a substituted or unsubstituted biphenyl group
- Cz is a substituted or unsubstituted carbazolyl group, and L may have a substituent.
- R represents a cyclic group or an aromatic heterocyclic group, and R to R each independently represent a hydrogen atom, a halogen atom,
- Atom alkyl group, aralkyl group, alkenyl group, cyano group, amino group, acyl group, alkoxycarbonyl group, carboxyl group, alkoxy group, aryloxy group, alkylsulfonyl group, hydroxyl group, amide group, aromatic hydrocarbon ring Represents a group or an aromatic heterocyclic group
- R to R are adjacent to each other
- L is an optionally substituted divalent aromatic group
- R represents a cyclic group or an aromatic heterocyclic group, and R to R each independently represent a hydrogen atom, a halogen atom,
- Atom alkyl group, aralkyl group, alkenyl group, cyano group, amino group, acyl group, alkoxycarbonyl group, carboxyl group, alkoxy group, aryloxy group, alkylsulfonyl group, hydroxyl group, amide group, aromatic hydrocarbon ring Represents a group or an aromatic heterocyclic group
- R to R are adjacent to each other
- an organic EL element having a low voltage, high efficiency, and long life can be realized by using a material having a special structure.
- FIG. 1 is a schematic cross-sectional view showing one embodiment of an organic EL device of the present invention.
- FIG. 2 is a schematic cross-sectional view showing another embodiment of the organic EL device of the present invention.
- the organic EL device of the present invention has a light emitting layer composed of at least an organic compound between an anode and a cathode. It has two or more layers in the hole injection / transport zone between the anode and the light emitting layer.
- FIG. 1 is a schematic cross-sectional view showing one embodiment of the organic EL device of the present invention.
- an anode 10 a hole injection layer 20, a hole transport layer 30, a light emitting layer 40, an electron transport layer 50, an electron injection layer 60, and a cathode 70 are laminated in this order on a substrate (not shown).
- the hole injection layer 20 and the hole transport layer 30 which are layers in the hole injection / transport zone satisfy the following conditions (A) and (B).
- the layer in contact with the light emitting layer contains a compound represented by the following formula (1)
- the layer (hole injection layer 20) between the anode and the layer in contact with the light emitting layer contains an amine derivative represented by the following formula (2).
- the driving voltage of the device is not increased, and the device has high luminous efficiency and long life.
- the compound of the above formula (1) and the amine derivative of the formula (2) in combination, the property of improving the efficiency of the device, which is unique to the compound of the formula (1), is maintained. This is probably because holes easily flow and the number of holes injected into the light-emitting layer increases dramatically. It is also thought that the layer of the compound of formula (1) prevents electrons from reaching the layer of the derivative of formula (2).
- Z is a substituted or unsubstituted nitrogen-containing heterocyclic group.
- pyrrole, imidazole, pyrazole, triazole, oxadiazole, pyridine, pyrazine, triazine, pyrimidine, carbazole, azacarbazole, diazacarbazole, indole, benzimidazole, imidazopyridine, indolizine and the like can be mentioned. More preferred are imidazole, carbazole, indole, indolizine, imidazopyridine, pyridine, pyrimidine and triazine.
- the substituent of Z includes a hydrogen atom, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom or an iodine atom), an alkyl group (for example, a methyl group, an ethyl group, etc .; straight chain having!
- a branched alkyl group a cycloalkyl group having 5 to 8 carbon atoms such as a cyclopentyl group or a cyclohexyl group
- an aralkyl group for example, a aralkyl group having 7 to 13 carbon atoms such as a benzyl group or a phenethyl group
- An alkenyl group eg, a straight chain or branched alkenyl group having 2 to 7 carbon atoms such as a bur group or an aryl group
- a cyan group an amino group, particularly a tertiary amino group (such as a jetyl amino group, a diisopropylamino group, etc.)
- Straight chain, branched or cyclic carbon atoms of! -20 carbons such as arylenorequinoleamino groups having 7 to 20 carbon atoms, acyl groups (eg acetyl, propionyl, benzoyl, naphthoyl, etc.)
- a hydrogen group-containing acyl group such as a linear or branched alkoxycarbonyl group having 2 to 7 carbon atoms such as a methoxycarbonyl group or an ethoxycarbonyl group), a carboxyl group, an alkoxy group ( For example, methoxy group, ethoxy group, etc., straight chain or branched alkoxy group having carbon number of 6 to 6), aryloxy group (for example, phenoxy group, benzyloxy group, etc., carbon number of 6 to 10; aryloxy group), alkylsulfonyl Groups (for example, methylsulfonyl group,
- a substituent for Z more preferably a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy Group, an aromatic hydrocarbon ring group, and an aromatic heterocyclic group.
- substituents may further have a substituent.
- substituents include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom or an iodine atom), an alkyl group (for example, a methyl group, an ethyl group).
- haloalkyl group for example, trifluoromethyl group or the like! Haloalkyl group
- cyan group a halogen atom, an alkoxy group, and an aromatic hydrocarbon ring group are more preferable.
- L represents a linking group formed by bonding 1 to 4 divalent aromatic groups which may have a substituent.
- L is
- Ar 1 ′, Ar 2 ′, Ar 3 ′, Ar 4 ′, Ar 6 ′, Ar 7 ′ and Ar 10 ′ may be substituted, and each of the aromatic rings having 5 to 6 members may be substituted.
- Ar 1, Ar 2 ', Ar 3', Ar 4 ', Ar. , Ar 7 and Ar 10 ′ specifically, a divalent aromatic hydrocarbon ring group such as a phenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a pyrenylene group, a perylene group, a pyridylene group, and a triadylene group
- divalent aromatic heterocyclic groups such as pyrazilene group, quinoxalylene group, chainylene group, and oxaziazolylene group.
- Ar 8 'and Ar 9 ' are forces that are divalent aromatic groups represented by the groups described above as Ar 1 'or the like, or NAr 11 '-(where Ar 11 'is And a divalent arylamino group represented by a monovalent aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have a substituent.
- Ar 11 ′ includes, for example, a 5- or 6-membered aromatic group such as a phenyl group, a naphthyl group, an anthryl group, a phenanthyl group, a chenyl group, a pyridyl group, a carbazolyl group, and the like. You may have.
- Ar 1 ' which is the smallest linking group as L, is preferably 3 or more condensed rings in order to improve the rigidity of the compound and the heat resistance resulting therefrom.
- a monocyclic ring or a 2-3 condensed ring is preferable, and a monocyclic ring or a 2-condensed ring is more preferable.
- A, Ar 8 'and Ar 9' from the viewpoint of improving the amorphous of Shi preferred that an aromatic ring ingredients of compound is, A, Ar 8 'And Ar 9 ' are preferably one NAr 11 '—.
- Ar 5 ′, Ar 8 ′ and Ar 9 ′ are preferably one NAr 11 ′ —.
- the emission wavelength of the compound can be slightly increased, and a desired emission wavelength can be easily obtained.
- the other is preferably an aromatic group.
- Examples of the substituent that Ar 1 ′ to Ar 1Q ′ may have include the same groups as those exemplified as the substituent for Z. Among these, an alkyl group, an alkoxy group, an aromatic hydrocarbon ring group, or an aromatic heterocyclic group is particularly preferable.
- substituent Ar 11 ' which may have, for example, include the same groups as those exemplified as the substituent of Z. Particularly preferred among these are an arylamino group, a phenyl group, and a naphthyl group. Or an aromatic heterocyclic group such as a carbazolyl group.
- Ar 1 and Ar 2 each independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have a substituent.
- Examples of the aromatic hydrocarbon ring group of Ar 1 and Ar 2 include a benzene ring monocyclic group or a group consisting of 2 to 5 condensed rings, and specifically include a phenyl group, a naphthyl group, an anthryl group, a phenyl group. Examples include an enanthryl group, a pyrenyl group, and a perylenyl group.
- Examples of the aromatic heterocyclic group include a 5- or 6-membered monocyclic ring or a 2-5 condensed ring, and specific examples include a pyridyl group, a triazinyl group, a birazinyl group, a quinoxalinyl group, and a chenyl group. .
- Examples of the substituent that the aromatic hydrocarbon ring group and the aromatic heterocyclic group may have include, for example, an alkyl group (for example, a linear or branched alkyl group having 1 to 6 carbon atoms such as a methyl group or an ethyl group).
- an alkyl group for example, a linear or branched alkyl group having 1 to 6 carbon atoms such as a methyl group or an ethyl group.
- an alkenyl group for example, a linear or branched alkenyl group having from 6 to 6 carbon atoms such as a vinyl group or an aryl group
- an alkoxycarbonyl group for example, a methoxycarbonyl group, an ethoxycarbonyl group, etc. 6 straight-chain or branched alkoxycarbonyl groups
- alkoxy groups for example, methoxy groups, ethoxy groups, etc .; C-6 linear or branched alkoxy groups
- aryloxy groups for example, phenoxy groups, naphthoxy groups.
- aryloxy group having 6 to 10 carbon atoms Such as aryloxy group having 6 to 10 carbon atoms), aralkyloxy group (for example, allyloxy group having 7 to 13 carbon atoms such as benzyloxy group), secondary or tertiary amino group (for example, For example, a dialkylamino group having a linear or branched alkyl group having 2 to 20 carbon atoms such as a jetylamino group or a diisopropylamino group; a diarylamino group such as a diphenylamino group or a phenylnaphthylamino group; a methylphenylamino group; Carbon atoms having 7 to 20 carbon atoms, halogen atoms (fluorine atoms, chlorine atoms, bromine atoms or iodine atoms), aromatic hydrocarbon ring groups (for example, phenyl groups, naphthyl groups, etc.) , Aromatic hydro
- alkyl groups alkoxy groups, anolenoreamino groups, arenoreamino groups, arylalkylamino groups, halogen atoms, aromatic hydrocarbon ring groups, and aromatic heterocyclic groups are preferred alkyl groups, Alkoxy groups and arylamino groups are particularly preferred.
- Ar 1 and Ar 2 are connected via two or more direct bonds, such as a terphenyl group. If the structure contains 3 or more aromatic groups, the hole transport ability of the arylamino group represented by NA ⁇ Ar 2 may be reduced, and the Tg of the compound may be reduced. it is conceivable that.
- Ar 1 and Ar 2 both have three or more aromatic groups connected in series via a direct bond or a short chain linking group. It is important that the bond is a V, a radical group.
- the nitrogen-containing heterocyclic derivative represented by the formula (1) is preferably a force rubazole derivative represented by the following formula (6).
- Cz is a substituted or unsubstituted carbazolyl group.
- Examples of the carbazolyl group represented by Cz include a 1-strength rubazolyl group, a 2-strength rubazolyl group, a 3-carbazolyl group, a 4-strength rubazolyl group, and an N-strand rubazolyl group.
- Preferred are a 2-canolebasolinole group, a 3-canolebasolinole group, and an N 2 rubazolyl group.
- These strong rubazolyl groups may have a substituent.
- substituents include the same substituents as Z in formula (1).
- L represents 1 to 4 divalent aromatic groups which may have a substituent.
- a linking group formed by bonding is represented.
- Preferred groups as L are the same as L in formula (1).
- Ar and Ar may each independently have a substituent.
- An aromatic hydrocarbon ring group or an aromatic heterocyclic group An aromatic hydrocarbon ring group or an aromatic heterocyclic group.
- Preferred groups for Ar and Ar are
- the force rubazole derivative of the formula (6) is preferably a compound containing an N force rubazolyl group represented by the following formula (7).
- Ar 1 and Ar 2 are each independently an aromatic hydrocarbon which may have a substituent.
- R represents a cyclic group or an aromatic heterocyclic group, and R to R each independently represent a hydrogen atom, a halogen atom,
- Atom alkyl group, aralkyl group, alkenyl group, cyano group, amino group, acyl group, alkoxycarbonyl group, carboxyl group, alkoxy group, aryloxy group, alkylsulfonyl group, hydroxyl group, amide group, aromatic hydrocarbon ring Represents a group or an aromatic heterocyclic group
- R to R are adjacent to each other
- L is an optionally substituted divalent aromatic group
- V represents a linking group formed by four bonds.
- R 6 to R 13 may be bonded together to form a ring condensed with an N-carbazolyl group.
- the ring formed by bonding of adjacent groups is usually a 5- to 8-membered ring, preferably a 5- or 6-membered ring, more preferably a 6-membered ring.
- this ring may be an aromatic ring or a non-aromatic ring, but is preferably an aromatic ring.
- it may be an aromatic hydrocarbon ring or an aromatic heterocyclic ring, but is preferably an aromatic hydrocarbon ring.
- N-force rubazolyl group of the formula (7) in which any of R 6 to R 13 are bonded to form a condensed ring bonded to the N-force rubazolyl group include the following: Can be mentioned.
- R 6 to R 13 are particularly preferably all hydrogen atoms (that is, the N-force rubazolyl group is unsubstituted), or one or more carboxylic groups, phenyl groups, or methoxy groups. This is the case where the rest are hydrogen atoms.
- the compound represented by the formula (7) is particularly preferably a compound represented by the following formula (8).
- examples of each group of R 6 to R 15 are the same as the above substituent of Z. They may be linked together to form a saturated or unsaturated ring.
- Ar and Ar each independently represent a substituent.
- An aromatic hydrocarbon ring group or an aromatic heterocyclic group which may be present is shown, and examples thereof are the same as Ar described above.
- a fluorene compound represented by the following formula (9) can also be preferably used.
- X is unsubstituted or substituted with a halogen atom, an alkyl having 1 to 10 carbon atoms; N-streptyl group, unsubstituted or substituted, which may be mono- or poly-substituted with an alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms, or a halogen as a substituent.
- a halogen atom an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 10 to 10 carbon atoms, an alkoxy group having 10 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms may be mono- or polysubstituted.
- halogen A mono- or poly-substituted mono- or poly-substituted by a thiol, an alkyl group, an alkoxy group, or an aryl group may be a carbocyclic aromatic group having 6 to 20 carbon atoms in total or a heterocyclic ring having
- B and B are a hydrogen atom, a linear, branched or cyclic alkyl group, unsubstituted, or
- a halogen atom, an alkyl group, an alkoxy group, or an aryl group is substituted or polysubstituted, and may be a carbocyclic aromatic group having 6 to 20 carbon atoms or 3 carbon atoms.
- Z is a hydrogen atom, halogen atom, straight chain, minute
- Bi- or cyclic alkyl groups linear, branched or cyclic alkoxy groups, or unsubstituted or substituted as mono- or poly-substituted with halogen atoms, alkyl groups, alkoxy groups, or aryl groups.
- ⁇ represents a substituted or unsubstituted N force rubazoyl group, a substituted or unsubstituted N phenoxazyl group, or a substituted or unsubstituted N phenothiazyl group, preferably As an unsubstituted or substituted group, for example, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 10 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms may be mono-substituted or poly-substituted.
- N force rubazyl group N phenoxazyl group, or N phenothiazyl group, more preferably unsubstituted, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.
- a group having 6 to 10 carbon atoms, which is monosubstituted, is polysubstituted may be, N is a rubazol group N phenoxazyl group, or N An enothiazyl group, more preferably an unsubstituted N 6 rubazoyl group, an unsubstituted N phenoxazyl group, or an unsubstituted N phenothiazyl group.
- substituted or unsubstituted N force rubazoyl group, the substituted or unsubstituted N phenoxyl group, or the substituted or unsubstituted N phenothiazyl group of X include, for example, an N force rubazoyl group, 2-methyl-N Forced rubazyl group, 3-methyl-N—forced rubazol group, 4-methyl-N forced rubazol group, 3-n-butyl-N forced rubazoyl group, 3-n hexylou N forced rubazyl group, 3—n-octylu-N-forced rubazol group, 3— n Decyl-N force rubazoyl group, 3,6 dimethyl-N force rubazoyl group, 2-methoxy-1-N force rubazoyl group, 3-methoxy-1-N-force rubazoyl group, 3-ethoxy-1-N-force rubazoyl group, 3-isopropoxy N force rubazoyl group 3-, n-but
- Norevazol group substituted or unsubstituted N phenoxazyl group, substituted or unsubstituted N-phenothiazyl group, or NAr 21 Ar 22 '(where Ar 21 ' and Ar 22 'are substituted or unsubstituted aryl groups) Represents).
- X substituted or unsubstituted N 6 rubazoyl group, substituted or unsubstituted N phenoxy Specific examples of the sadyl group and the substituted or unsubstituted N phenothiazyl group include, for example, the substituted or unsubstituted N force rubazoyl group, substituted or unsubstituted N phenoxazyl group, substituted or unsubstituted N Refers to the power to illustrate the phenothiazyl group.
- Ar 21 ′ and Ar 22 ′ represent a substituted or unsubstituted aryl group.
- the aryl group represents a carbocyclic aromatic group such as a phenyl group, a naphthyl group, and an anthryl group, for example, a heterocyclic aromatic group such as a furyl group, a chenyl group, and a pyridyl group.
- Ar 21 ′ and Ar 22 ′ are preferably unsubstituted or monosubstituted or polysubstituted by a substituent such as a halogen atom, an alkyl group, an alkoxy group, or an aryl group.
- Ar 21 'and Ar 22 include, for example, a phenyl group, a 1 naphthyl group, a 2 naphthyl group, a 2 anthryl group, a 9 anthryl group, a 4-quinolinole group, a 4 pyridinole group, a 3 pyridinole group, 2 pyridinole group, 3 frinole group, 2 frinole group, 3 cheninole group, 2 cheninole group, 2-oxazolyl group, 2-thiazolyl group, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benen Zoimidazolyl group, 4 methylphenyl group, 3 methylphenyl group, 2 methylphenyl group, 4 ethenylphenyl group, 3 ethenylphenyl group, 2 ethenylphenyl group, 4-n propylphenyl group, 4 isopropylphen
- B and B are a hydrogen atom, a straight chain, a branched chain or a ring.
- carbon number represents a substituted or unsubstituted aryl group having 4 to 16 or a substituted or unsubstituted aralkyl group having 5 to 16 carbon atoms, more preferably a hydrogen atom, a carbon number;!
- B and B are carbon atoms;! -8 to linear, branched or cyclic alkyl groups, carbon atoms
- substituted or unsubstituted aryl group of B and B include, for example, Ar
- linear, branched or cyclic alkyl group for B and B include, for example,
- Methyl group, ethyl group, n propyl group, isopropyl group, n butyl group, isobutyl group, sec butyl group, tert butyl group, n pentyl group, isopentyl group, neopentinole group, tert pentyl group, cyclopentyl group, n hexyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, cyclohexyl group, n-heptyl group, cyclohexylmethyl group, n-octyl group, tert-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group , N-dodecyl group, n-tetradecyl group, n-hexadecyl group, and the like are not limited thereto.
- substituted or unsubstituted aralkyl group of B and B include, for example,
- Benzyl group phenethyl group, ⁇ methylbenzyl group, ⁇ , a-dimethylbenzyl group, 1 naphthylmethyl group, 2 naphthylmethyl group, furfuryl group, 2 methylbenzyl group, 3 methylbenzyl group, 4 methylbenzyl group, 4 ethenylbenzyl group , 4 isopropylenovenenore group, 4 tert butinoleveninore group, 4-n hexenolevendinole group, 4-noni Norebendyl group, 3,4-dimethylbenzyl group, 3-methoxybenzyl group, 4-methoxybenzenole group, 4 ethoxybenzyl group, 4-n-butoxybenzyl group, 4-n hexyloxybenzyl group, 4-noeroxy Forces that can include aralkyl groups such as benzyl group, 4-fluorobenzyl group, 3-fluorobenzyl group,
- Z and Z are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a straight
- linear, branched or cyclic alkyl group of Z and Z include, for example,
- the force S can be used to indicate the substituted or unsubstituted aryl groups listed as specific examples of Ar 21 ′ and Ar 22 ′.
- a halogen atom such as a fluorine atom, a chlorine atom or a bromine atom, such as a methoxy group, an ethoxy group, a ⁇ propoxy group, an isopropoxy group, a ⁇ butoxy group, an isobutoxy group, a sec butoxy group, an n pentyloxy group, or an isopentyl group.
- nitrogen-containing heterocyclic derivatives that can be used in the present invention are shown below.
- L is a substituted or unsubstituted arylene group having 10 to 40 carbon atoms.
- Ar to Ar in the formula (2) are each substituted or unsubstituted aromatic carbon having 6 to 60 nuclear carbon atoms.
- the cyclic group is the same as Ar and Ar in formula (1).
- Examples of the substituted or unsubstituted aromatic heterocyclic group having 6 to 60 nuclear atoms include, for example, a 5- or 6-membered monocyclic ring or a 2 to 5 condensed ring. Specific examples include a pyridyl group and a triazinyl group. Group, birazinyl group, quinoxalinyl group and chenyl group.
- the amine derivative of the formula (2) is preferably a compound represented by the following formula (3).
- Ar to Ar are the same as Ar to Ar in Formula (2).
- R represents a substituent. Specific examples of R are the same as the above-described substituents such as Z in the formula (1).
- n an integer of 2 to 4. 2 and 3 are preferred.
- the amine derivative represented by the formula (2) is more preferably a compound represented by the following formula (4) or (5).
- R to R are substituents, and specific examples are the same as R in the formula (3).
- R to R may combine with each other to form a saturated or unsaturated ring.
- Ar to Ar are each a substituted or unsubstituted aromatic group having 6 to 60 nuclear carbon atoms.
- Ar to Ar include those similar to Ar and Ar in formula (1).
- R to R are preferably the same as the substituents such as Z in formula (1) Is mentioned. R and R are bonded together to form a substituted or unsubstituted ring.
- One is preferably a substituted or unsubstituted biphenyl group.
- the arylamine group may be substituted at the end of this substituted or unsubstituted biphenyl group.
- the layer in contact with the anode of the layer in the hole injection / transport zone is preferably a layer containing an acceptor material.
- FIG. 2 is a schematic cross-sectional view showing another embodiment of the organic EL device of the present invention.
- the organic EL element in FIG. 2 is the same as the organic EL element in FIG. 1 except that an acceptor-containing layer 80 is provided between the anode 10 and the hole injection layer 20.
- the voltage can be reduced.
- the acceptor is an easily reducible organic compound.
- the reduction potential using a saturated calomel (SCE) electrode as a reference electrode is preferably 0.8 V or more, particularly preferably a value greater than the reduction potential (about 0 V) of tetracyanoquinodimethane (TCNQ).
- SCE saturated calomel
- TCNQ tetracyanoquinodimethane
- the easily reducible organic compound is preferably an organic compound having an electron-withdrawing substituent.
- Specific examples include quinoid derivatives, pyrazine derivatives, arylborane derivatives, imide derivatives, and the like.
- the quinoid derivatives include quinodimethane derivatives, thiopyran dioxide derivatives, thioxanthene dioxide derivatives, quinone derivatives, and the like.
- the quinoid derivative preferably includes compounds represented by the following formulas (la) to (; li). More preferred are compounds represented by (la) and (lb).
- Fluorine and chlorine are preferred as halogens for I ⁇ R 48 .
- a trifluoromethyl group and a pentafluoroethyl group are preferable.
- the aryl group of I ⁇ R 48 is preferably a phenyl group or a naphthyl group.
- X is an electron withdrawing group, and has one of the structures of the following formulas (1) to (p). Preferably, it is the structure of (1), (k), (1).
- R 49 to 2 are each hydrogen, a fluoroalkyl group, an alkyl group, an aryl group, or a heterocyclic ring, and R 5 ° and R 51 may form a ring.
- the fluoroalkyl group, alkyl group, and aryl group of R 49 to R 52 are the same as I ⁇ R 48.
- heterocyclic ring R 49 to R 52 preferably a substituted group represented by the following formula.
- X is preferably a substituent represented by the following formula.
- R 1 and R 2 are a methyl group, an ethyl group, a propyl group, and a tert butyl group, respectively.
- quinoid derivative include the following compounds.
- Examples of the arylporane derivative include compounds represented by the following formula (2).
- Ar 1 to Ar 3 are each an aryl group having an electron withdrawing group or
- pentafluorophenol As an aryl group having an electron-withdrawing group represented by Ar to Ar, pentafluorophenol is used.
- the ru group heptafluoronaphthyl group and the pentafluorophenyl group are preferred.
- a heterocyclic ring having an electron-withdrawing group represented by Ar to Ar a quinoline ring or a quinoxaline ring
- a pyridine ring, a pyrazine ring and the like are preferable.
- arylborane derivatives include the following compounds.
- aryl borane derivative a compound having at least one fluorine as a substituent to the aryl is preferable, and tris ⁇ (pentafluoronaphthyl) borane ( ⁇ ) is particularly preferable.
- Examples of the thiopyran dioxide derivative include a compound represented by the following formula (3a), and examples of the thioxanthene dioxide derivative include a compound represented by the following formula (3b).
- R 1 to R 5 are each hydrogen, halogen, a fluoroalkyl group, a cyano group, an alkyl group, or an aryl group. Of these, hydrogen and cyano group are preferable.
- X represents an electron withdrawing group and is the same as X in the formulas (la) to (; li).
- the structures (i), (1) and (k) are preferred.
- ⁇ 1 is the same as that of the ⁇ R 48.
- Specific examples of the thiopyran dioxide derivative represented by the formula (3a) and the thioxanthene dioxide derivative represented by the formula (3b) are shown below.
- tBu is a t-ptel group.
- the imide derivative is preferably a naphthalene tetracarboxylic acid diimide compound or a pyromellitic acid diimide compound.
- each of R 121 to R 12b represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group.
- R 121 to R 126 may be the same or different, R 121 and R 122 , R 123 and R 124 , R 125 and R 126 , R 121 and R 126 , R 122 and R 123 , R 124 and R 125 may form a condensed ring.
- R 131 to R 136 are substituents, and preferably an electron-withdrawing group such as cyan group, nitro group, sulfonyl group, force sulfonyl group, trifluoromethyl group, and halogen.
- 1 to are hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic ring, a halogen, a cyano group, a nitro group, an ester group, It is selected from the group consisting of an amide group, an alkoxy group, a substituted or unsubstituted phenoxy group and an amino group, which may be the same or different.
- adjacent ones of R 81 to R 88 may be bonded to each other to form a ring structure.
- X 81 to x 84 are each independently a carbon atom or a nitrogen atom, and n is an integer of 0 or more.
- FIG. 2 Anode / acceptor containing layer / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (FIG. 2)
- the light emitted from the light-emitting layer is measured by the force of taking out from one side or both sides of the anode side and the cathode side.
- the organic EL element may have a cavity structure between the anode and the cathode, that is, a structure in which light emitted from the light emitting layer is reflected between the anode and the cathode.
- the cathode is configured using a semi-transmissive / semi-reflective material and has a light reflecting surface of the anode. In this case, light emitted by multiple interference between the light reflecting surface on the anode side and the light reflecting surface on the cathode side is extracted from the cathode side.
- the optical distance between the light reflecting surface on the anode side and the light reflecting surface on the cathode side is defined by the wavelength of light to be extracted, and the film thickness of each layer is set so as to satisfy this optical distance.
- the active use of this cavity structure improves the light extraction efficiency to the outside and the emission spectrum. It is possible to perform control.
- the organic EL device of the present invention is manufactured on a light-transmitting substrate.
- the light-transmitting substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 to 700 nm of 50% or more.
- a glass plate, a polymer plate, etc. are mentioned.
- the glass plate include soda-lime glass, norlium strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, norium borosilicate glass, and quartz.
- the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyethersulfide, and polysulfone.
- the substrate does not necessarily need to be translucent.
- the anode of the organic thin film EL element plays a role of injecting holes into the hole transport layer or light emitting layer. It is effective to have a work function of 4.5 eV or more.
- Specific examples of anode materials used in the present invention include, for example, aluminum (A1), chromium (Cr), molybdenum (Mo), tungsten (W), copper (Cu), silver (Ag), and gold (Au).
- ITO indium tin oxide
- InZnO indium zinc oxide
- alloys of zinc oxide (Z ⁇ ) and aluminum (A1) and oxides of these metals and alloys alone or mixed Used in
- the transmittance S of the light emitted from the anode is preferably greater than 10%.
- the anode when light emitted from the light emitting layer is extracted from the cathode, the anode is preferably a reflective electrode.
- the anode may have a laminated structure of a first layer having excellent light reflectivity and a second layer having a light transmissivity and a high work function provided on the upper layer.
- the first layer is made of an alloy containing aluminum as a main component.
- the subcomponent may include at least one element having a work function relatively smaller than that of aluminum as a main component.
- a lanthanoid series element is preferable.
- the work function of lanthanoid series elements is not large, the inclusion of these elements improves the stability of the anode and also satisfies the hole injection property of the anode.
- elements such as silicon (Si) and copper (Cu) may be included as subcomponents.
- the content of subcomponents in the aluminum alloy layer constituting the first layer is, for example, about 10 wt% or less in total for Nd, Ni, Ti, or the like that stabilizes aluminum. preferable.
- the aluminum alloy layer can be stably maintained in the manufacturing process of the organic electroluminescent device, and further, accuracy and chemical stability can be obtained.
- the conductivity of the anode and the adhesion to the substrate can be improved.
- the second layer can be exemplified by a layer comprising at least one of an aluminum alloy oxide, a molybdenum oxide, a zirconium oxide, a chromium oxide, and a tantalum oxide.
- the second layer is an oxide layer (including a natural oxide film) of an aluminum alloy containing a lanthanoid element as a subsidiary component, the transmittance of the oxide of the lanthanoid element is Since it is high, the transmittance of the second layer including this is good. For this reason, it is possible to maintain a high reflectivity on the surface of the first layer.
- the second layer may be a transparent conductive layer such as ITO or IZO. These conductive layers can improve the electron injection characteristics of the anode.
- a conductive layer for improving the adhesion between the anode and the substrate may be provided on the side of the anode in contact with the substrate.
- a conductive layer include transparent conductive layers such as ITO and IZO.
- the driving method of the display device configured using the organic EL element is the active matrix method
- the anode is patterned for each pixel and connected to the driving thin film transistor provided on the substrate. It is provided in the state.
- an insulating film is provided on the anode, and the surface of the anode of each pixel is exposed from the opening of the insulating film.
- the anode is measured by the force of forming the electrode material described above by forming a thin film by a method such as vapor deposition or sputtering.
- the sheet resistance of the anode is preferably several hundred ⁇ / mouth or less.
- the film thickness of the anode depends on the material, it is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 to 200 nm.
- the light emitting layer of the organic EL device has the following functions.
- Injection function A function capable of injecting holes from the anode or hole injection / transport layer when an electric field is applied, and an electron from the cathode or electron injection / transport layer
- Transport function Function to move injected charges (electrons and holes) by the force of electric field
- Light-emitting function A function that provides a field for recombination of electrons and holes and connects it to light emission. However, there is a difference between the ease of hole injection and the ease of electron injection.
- the transport ability expressed by the mobility of electrons may be large or small, but it is preferable to move one of the charges.
- the light emitting layer for example, a known method such as a vapor deposition method, a spin coating method, or an LB method can be applied.
- the light emitting layer is particularly preferably a molecular deposited film.
- the molecular deposition film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidification from a material compound in a solution state or a liquid phase state.
- a film can be classified from a thin film (accumulated film) formed by the LB method by the difference in aggregated structure and higher-order structure and functional differences resulting from it.
- a binder such as a resin and a material compound are dissolved in a solvent to form a solution, which is then thinned by a spin coating method or the like. By doing so, the light emitting layer can be formed.
- the material used for the light-emitting layer is a force capable of using a known light-emitting material having a long lifetime, and the material represented by the general formula (I) is preferably used as the light-emitting material.
- Ar ′ is an aromatic ring having 6 to 50 nuclear carbon atoms or a heteroaromatic ring having 5 to 50 nuclear atoms.
- Preferred examples include a phenyl ring, a naphthyl ring, an anthracene ring, a acenaphthylene ring, a fluorene ring, a phenanthrene ring, a fluoranthene ring, a triphenylene ring, a pyrene ring, a taricene ring, a benzanthracene ring, and a perylene ring.
- X ' is a substituent. Specifically, a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted or unsubstituted carbon group having 1 to 50 carbon atoms.
- Alkyl group substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 1 to 50 carbon atoms, substituted or unsubstituted arylenoxy group having 5 to 50 nuclear atoms, substituted or An unsubstituted aryl group having 5 to 50 nuclear atoms, a substituted or unsubstituted carboxyl group having 1 to 50 carbon atoms, a substituted or unsubstituted styryl group, a halogen group, a cyano group, a nitro group, a hydroxyl group, and the like.
- Examples of the substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms include phenyl group, 1 naphthyl group, 2-naphthyl group, 1 anthrinol group, 2-anthrinol group, 9 anthrinol group, 1 phenanthrinol group.
- a phenyl group Preferably a phenyl group, a 1 naphthyl group, a 2 naphthyl group, a 9 phenanthryl group, a 1-naphthacenyl group, a 2 naphthacenyl group, a 9 naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenyl group Ruyl group, 3-biphenylyl group, 4-biphenylolenoreole group, o-trinore group, m-trinole group, p-trinole group, p-t butylphenyl group, 2-phenololenyl group, 9, 9 dimethyl-2-fluorenyl group, 3 full Orantenyl group isotropic force.
- Examples of the substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms include 1 pyrrolyl group, 2 pyrrolyl group, 3 pyrrolyl group, birazinyl group, 2 pyridinyl group, 3 pyridinyl group.
- substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, and n-pentyl group.
- a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms is a group represented by OY.
- Y include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, and isobutyl.
- substituted or unsubstituted aralkyl groups having 1 to 50 carbon atoms include benzyl group, 1 phenylethyl group, 2-phenylethyl group, 1 phenylisopropyl group, 2-phenylisopropyl group, and phenyl-butyl group.
- ⁇ -naphthylmethyl group 1 ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1-a naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1; 3-naphthylethyl group, 2 ⁇ -naphthylethyl group, 1 — ⁇ naphthyl isopropyl group, 2— ⁇ naphthyl isopropyl group, 1 pyrrolylmethyl group, 2 (1 pyrrolyl) ethyl group, ⁇ methylbenzyl group, m-methinolevendinore group, o methinolevendinore group, p-clonal benzoinole group , M-black benzenore group, o black benzyleno group, p bromobenzenole group
- a substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms is represented as OY ', and examples of Y' include phenyl group, 1 naphthyl group, 2-naphthyl group, 1 anthryl group, 2-anthrinole group, 9 N-trinole group, 1-Phenanthrinol group, 2-Phenanthrinol group, 3-Phenanthrinol group, 4- Phenanthrinol group, 9- Phenanthrinol group, 1-Naphthacenino group, 2-Naphthacenyl group, 9- Naphthenyl group, 1-Pyrenyl group, 4-Pyrenyl group Group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, ⁇ -terfeninore 4-inole group, ⁇ terfeninole 3-inole group, ⁇
- a substituted or unsubstituted arylylthio group having 5 to 50 nuclear atoms is represented by SY ", and examples of Y" include phenyl, 1 naphthyl, 2-naphthyl, 1 anthryl, 2-antholinole, 9 Ntrinole group, 1 Phenanthrinol group, 2 Phenanthrinol group, 3 Phenanthryl group, 4 Phenanthrinol group, 9 Phenanthrinol group, 1 Naphthalcenyl group, 2 Naphthacin binole group, 9 Naphthenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group , 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terferyl group
- a substituted or unsubstituted carboxyl group having 1 to 50 carbon atoms is represented as COOZ ′, and examples of Z ′ include methyl group, ethyl group, propyl group, isopropyl group, n butyl group, s butynole group, isobutyl group, t butyl group, n pentyl group, n hexyl group, n heptyl group, n octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxy Ethyl group, 1,3-dihydroxyisopropyl group, 2,3 dihydroxy-t butyl group, 1,2,3 trihydroxypropyl group, chloromethyl group, 1 chloroethyl group, 2 chloroethyl group, 2— Black and white isobutyl group, 1,2 Dichlorodiethyl group, 1,3 Dichlorodie
- substituted or unsubstituted styryl groups include 2 phenyl 1-bule group, 2, 2 diphenyl 1-bule group, 1, 2, 2-triphenyl 2 1-bule group, etc. Is mentioned.
- nitrogen and rogen groups examples include fluorine, chlorine, bromine, iodine and the like.
- n is an integer of 0 to 6.
- n is preferably 0-4.
- Ar 'in () may be the same or different.
- X 'in () may be the same or different.
- the material used for the light emitting layer is more preferably an anthracene derivative shown below.
- A1 and A2 each represent a substituted or unsubstituted monophenylanthryl group or a substituted or unsubstituted diphenylanthryl group, and they may be the same or different. Represents a bond or a divalent linking group.
- An represents a substituted or unsubstituted divalent anthracene residue
- A3 and A4 each represent a substituted or unsubstituted monovalent fused aromatic ring group or a substituted or unsubstituted carbon group having 12 or more carbon atoms.
- Non-fused ring system aryl groups which may be the same or different from each other.
- Examples of the anthracene derivative represented by the formula (II) include an anthracene derivative represented by the following formula (II a),
- R 91 to R 1Q ° each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an optionally substituted aryl group, an alkoxyl group, an aryloxy group, an anolequinolamino group, an arylamine group
- a and b each represent an integer of;!
- R 91s or R 92s may be the same in each case R 91 and R 92 may be combined to form a ring, and R 93 and R 94 , R 95 and R 96 , R 97 and R 98 , R 99 and R 1Q ° may be bonded to each other to form a ring L 1Q is a single bond or —O—, —S—, —N (R) — (where R is an alkyl group or a substituted group) Or an arylene group.)
- R to R each independently represent a hydrogen atom, an alkyl group, or a cycloalkyl group.
- a substituted or unsubstituted aryl group, alkoxyl group, aryloxy group, alkylamino group, aryl group, or substituted or unsubstituted heterocyclic group, c, d, e and f are each an integer of 1 to 5 shown, when they are 2 or more, each other R 1Q1, among R 1Q2, R 1Q6 the mechanic or R 1 () 7 each other, in each Yogumata R 1Q1 together be the same or different, R 1Q2 together, R 1Q6 or R 1Q7 may be bonded together to form a ring, or R 1Q3 and R " 3 4 , R 1QS and R 1Q9 may be bonded together to form a ring.
- 11 represents a single bond or —O—, —S—, —N (R) — (wherein R represents an alkyl group or
- alkyl group represented by R in 1 N (R) — of L 1Q and L 11 is preferably an alkyl group having! To 6 carbon atoms, and the aryl group having 5 to 18 carbon atoms is preferable.
- Ar is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms.
- Ar ′ is a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms.
- ⁇ To ⁇ 3 Are independent In addition, there is no substitution or non-substitutional nuclear aromatic carbon group having a carbon number of 66 to 5500, no substitution, or no substitution.
- Substituting nuclear proatomic atoms 55--5500 aromatic-aromatic polyheterocyclic ring radicals, substitutional or non-substitutional carbons An aralkyloxyl group having a prime number of 11 to 5500, an unsubstituted or unsubstituted aralkyloxy group having a carbon number of 11 to 5500, and a substitution group. Possibly or non-substituted carbon atoms with 66 to 5500 carbon atoms, a non-substituted nuclear nucleus.
- R′-R 10 independently of each other, a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, substituted Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted C 6-50 carbon atomolequinole; Group, substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms, substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, substituted or unsubstituted Substituted silyl group, carboxy Group, hal
- Ar and Ar ′ each represent a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms.
- L and L ′ are each a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted dibenzosilolylene group.
- n is an integer from 1 to 4
- s is an integer from 0 to 2
- t is an integer from 0 to 4.
- L or Ar is bonded to any one of positions 1 to 5 of pyrene, and L ′ or Ar ′ is bonded to pyrene.
- a 1 and ⁇ ⁇ are each independently a substituted or unsubstituted condensed aromatic ring group having 10 to 20 nuclear carbon atoms.
- Ar 1 and Ar 2 are each independently a hydrogen atom or a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms.
- R′-R 10 independently of each other, a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, substituted Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted C 6-50 carbon atomolequinole; Group, substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms, substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, substituted or unsubstituted Substituted silyl group, carboxyl group,
- R 9 and R 1Q may be plural or adjacent to each other to form a saturated or unsaturated cyclic structure.
- a small amount of a fluorescent compound is added as a dopant to improve the light emitting performance. It is possible to make it.
- a dopant it is possible to use a known material as a long-life luminescent material, and it is desirable to use a material represented by the following formula (VI) as a dopant material of the luminescent material.
- Ar 41 to Ar 4 are substituted or unsubstituted aromatic groups having 6 to 50 nuclear carbon atoms, or substituted or unsubstituted styryl groups.
- Examples of the substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms include phenyl group, 1 naphthyl group, 2 naphthyl group, 1 anthrinol group, 2 anthrinol group, 9 anthrinol group, 1 phenanthrinol group, 2 phenanthrinol groups, 3 phenanthrinol groups, 4 phenanthrinol groups, 9 phenanthryl groups, 1 naphthacenyl groups, 2 naphthacenyl groups, 9 naphthacenyl groups, 1-pyrenyl groups, 2 pyrenyl groups, 4-pyrenyl groups, 2 biphenylolyl groups, 3 biphenylenoyl groups , 4-biphenylenoreino group, p terfeninore 4-inole group, p terfeninore 3 inole group, p terfeninore 2-
- substituted or non-substituted styryl groups examples include 2-phenol 2-l-bule group, 2, 2-diphenyl 2-bule group, 1, 2, 2-triphenyl 2-l-bule group, etc. Can be mentioned.
- p is an integer of 1 to 4.
- Ar 42 and Ar 43 in () may be the same or different.
- the hole injection / transport layer is a layer that helps to inject holes into the light emitting layer and transports them to the light emitting region.
- the ionization energy with high hole mobility is usually as low as 5.6 eV or less.
- a material that transports holes to the light emitting layer with a lower electric field strength is preferable.
- the mobility of holes is, for example, 10 4 to 10 6 V / cm. Sometimes preferred, if at least 10 _ 4 cm 2 / V ⁇ sec.
- the hole injection layer and the hole transport layer may each be a plurality of layers.
- the compounds of the above formulas (1) and (2) used in the device structure of the present invention may form a hole injection layer and a transport layer alone, or may be used by mixing with other materials. Also good.
- the material for forming the hole injection and transport layer by mixing with the compounds of the formulas (1) and (2) used in the device configuration of the present invention has the above-mentioned preferable properties. If there is no particular limitation, select any one of those conventionally used as a hole charge transport material in a photoconductive material or a known medium force used for a hole injection layer of an EL element. Can be used. In addition to the aromatic amine derivative layer and the nitrogen-containing heterocyclic derivative layer, there may be a layer constituting the hole transport zone, and any material can be selected from the known materials as described above. Can be selected and used. A compound represented by the following formula can be considered as the aromatic amine derivative.
- Ar to Ar b , Ar bl to Ar, Ar to Ar each represents a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms or a heteroaromatic group having 5 to 50 nuclear atoms, a to c and p to r are integers of 0 to 3, respectively, Ar 57 and Ar 58 , Ar 59 and Ar 6 °, Ar 61 and Ar 62 are connected to each other to form a saturated or unsaturated ring. May be.
- Ar to Ar 74 represent a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms or a heteroaromatic group having 5 to 50 nuclear atoms
- L 12 is a linking group, a single bond, or a substituted group.
- it represents a substituted aromatic group having 6 to 50 nuclear carbon atoms or a heteroaromatic group having 5 to 50 nuclear atoms
- X is an integer of 0 to 5
- Ar 72 and Ar 73 are linked to each other. To form a saturated or unsaturated ring.
- the material of the hole injection layer As the material of the hole injection layer, the above can be used, the porphyrin compound (Disclosed in JP-A-63-295695 etc.), aromatic tertiary amine compounds and styrylamine compounds (US Pat. No. 4,127,412, JP-A-53-27033) No. 54-58445, No. 55-79450, No. 55-144250, No. 56 119132, No. 61-295558, No. 61-98353, No. 63-2956 95, etc. In particular, it is preferable to use an aromatic tertiary amine compound.
- US Pat. No. 5,061,569 has two condensed aromatic rings in the molecule, for example, 4,4,1bis (N— (1-naphthyl) N phenylamino) biphenyl ( (Hereinafter abbreviated as NPD) and three, 4-, 4-, 4-"-tris (N- (3— Methyl phenyl) N phenylamino) triphenylamine (hereinafter abbreviated as MTDATA).
- R ll to R 1 b are each a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group.
- R 121 to R 126 may be the same or different, and R 121 and R 122 , R 123 and R 124 , R 125 and R 126 , R 121 and R 126 , R 122 and R 123 R 124 and R 125 may form a condensed ring.
- R 1dl R is a substituent, preferably an electron-withdrawing group such as a cyano group, a nitro group, a sulfonyl group, a force sulfonyl group, a trifluoromethyl group, or a halogen.
- acceptor materials can also be used as hole injection materials. Specific examples of these are as described above.
- inorganic compounds such as p-type Si p-type SiC can also be used as the material for the hole injection layer.
- the hole injection and transport layer can be formed by thinning the above-described compound by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method.
- the thickness of the hole injection / transport layer is not particularly limited, but is usually 5 nm 5 / im.
- this hole injection / transport layer contains the compound of the present invention in the hole transport zone, it may be composed of one or more of the above-mentioned materials, or the hole injection.
- a hole injection and transport layer made of a compound different from the transport layer may be laminated.
- An organic semiconductor layer may be further formed.
- This layer is a layer for helping the injection of holes or electron injection into the light emitting layer, is preferably one having a conductivity of more than 10_ 1Q S / cm.
- Examples of the material for such an organic semiconductor layer include thiophene oligomers, conductive oligomers such as allylamin oligomers disclosed in JP-A-8-193191, and arylamine amine dendrimers. A conductive dendrimer or the like can be used.
- the electron injection layer is a layer that assists the injection of electrons into the light emitting layer and has a high electron mobility.
- the adhesion improving layer is a layer made of a material having a particularly good adhesion to the cathode in the electron injection layer.
- a metal complex of 8-hydroxyquinoline or a derivative thereof is suitable.
- metal complexes of the above 8-hydroxyquinoline or its derivatives include oxine.
- metal chelate oxinoid compounds containing a chelate generally 8-quinolinol or 8-hydroxyquinoline.
- Alq described in the section of the light emitting material can be used as the electron injection layer.
- examples of the oxadiazole derivative include an electron transfer compound represented by the following general formula.
- a 1 , Ar 1 , Ar 1 , Ar 2, Ar 3, and ⁇ each represent a substituted or unsubstituted aryl group, and may be the same or different from each other.
- Ar 84 , Ar 87 , and Ar 88 are A substituted or unsubstituted arylene group, each of which may be the same or different)
- Examples of the aryl group include a phenyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group.
- Examples of the arylene group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group.
- Examples of the substituent include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 10 to 10 carbon atoms, and a cyan group.
- This electron transfer compound is preferably a film-forming compound.
- electron transfer compound examples include the following.
- nitrogen-containing heterocyclic derivatives represented by the following formulas (A) and (B) can be used as materials used for the electron injection layer.
- a 1 to A each independently represents a nitrogen atom or a carbon atom.
- Ar 21 is a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 nuclear carbon atoms
- Ar 22 is a hydrogen atom, substituted or unsubstituted Aryl group having 6 to 60 nuclear carbon atoms, substituted or unsubstituted nuclear carbon having 3 to 60 carbon atoms
- a teloaryl group a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, or a divalent group thereof.
- any one of Ar 21 and Ar 22 is a substituted or unsubstituted condensed ring group having 10 to 60 nuclear carbon atoms, a substituted or unsubstituted monoheterocondensed ring group having 3 to 60 nuclear carbon atoms, or These are divalent groups.
- Ar 23 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms.
- L u , L 12 and L 13 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 nuclear carbon atoms, or A substituted or unsubstituted fluorenylene group.
- R 81 is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 nuclear carbon atoms, a substituted or unsubstituted carbon number of 1 to 2
- R 82 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 nuclear carbon atoms, a substituted or unsubstituted carbon number of 1 to 2
- HAr is substituted a nitrogen-containing heterocyclic ring which may having 3 to 40 carbon atoms
- L 1 4 is a single bond
- a good number of carbon atoms from 6 may have a substituent 60 Ariren group, Les substituted, also good Le
- Re has a heteroarylene group or substituent to the 3 to 60 carbon atoms, it may also be a full Oreniren group
- Ar 24 Is a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent
- Ar 25 is an aryl group having 6 to 60 carbon atoms which may have a substituent or A heteroaryl group having 3 to 60 carbon atoms which may have a substituent.
- X 11 and Y 11 are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a hydroxy group, Or an unsubstituted aryl group, a substituted or unsubstituted hetero ring, or a structure in which X 11 and ⁇ 11 are combined to form a saturated or unsaturated ring, and R 85 to R 88 are each independently a water group.
- Atoms halogen atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, alkoxy groups, aryloxy groups, perfluoroalkyl groups, perfluoroalkoxy groups, amino groups, alkylcarbonyl groups, alkyl groups.
- R 91 to R 98 and Z 2 are each independently a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aromatic group, a heterocyclic group, a substituted amino group, a substituted boryl group, an alkoxy group.
- Group or Ali ⁇ 12 , Y 12 and Z 1 each independently represents a saturated or unsaturated hydrocarbon group, aromatic group, heterocyclic group, substituted amino group, alkoxy group or aryloxy group; Z 1 and Z 2 substituents may be bonded to each other to form a condensed ring.
- N represents an integer of !! to 3; when n is 2 or more, Z 1 may be different.
- n includes 1, X 12 , Y 12 and R 92 are methyl groups, and R 98 is a hydrogen atom or a substituted boryl group, and n is 3 and a Z force S methyl group. Absent.
- Q 1 and Q 2 each independently represent a ligand represented by the following formula (G), and L 15 represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted group Substituted cycloalkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, -OR (where R is a hydrogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted Or an unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.) Or —O—Ga—Q 3 (Q 4 ) (Q 3 and Q 4 are the same as Q 1 and Q 2 ) Represents a ligand. ]
- rings A 4 and A b are 6-membered aryl structures fused to each other which may have a substituent.
- This metal complex is strong as an n-type semiconductor and has a high electron injection capability. Furthermore, since the generation energy at the time of complex formation is low, the bond between the metal and the ligand of the formed metal complex is strengthened, and the fluorescence quantum efficiency as a light emitting material is also increasing.
- substituents of the rings A and A 25 forming the ligand of the formula (G) include chlorine, bromine, iodine, halogen atoms of fluorine, methyl group, ethyl group, propyl group, butyl group S butyl group t butyl group pentyl group hexyl group heptyl group octyl group stearyl group trichloromethyl group substituted or unsubstituted alkyl group phenyl group naphthyl group 3-methylphenyl group Substituted or unsubstituted aryl groups such as 3-methoxyphenyl group, 3-fluorophenyl group, 3 trichloromethylphenyl group, 3-trifluoromethylphenyl group, 3-nitrophenyl group, methoxy group , N-butoxy group, t-butoxy group, trichloromethoxy group, trifnoreo mouth ethoxy group, pent
- a 6-membered aryl ring or a heterocyclic ring may be formed.
- it may be a polymer compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative.
- a preferable embodiment of the present invention is an element containing a reducing dopant in an electron transporting region or an interface region between a cathode and an organic layer.
- the reducing dopant is defined as a substance capable of reducing an electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals.
- One substance can be preferably used.
- preferable reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), and Cs (work Function: 1. 95 eV)
- At least one alkali metal selected from the group of forces, Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2. 52 eV) force at least one alkaline earth metal selected from the group consisting of those having a work function of 2.9 eV or less is particularly preferred.
- a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb and Cs, more preferably Rb or Cs, and most preferably Cs. is there.
- alkali metals can improve emission brightness and extend the lifetime of organic EL devices by adding a relatively small amount to the electron injection region, which has a particularly high reducing ability.
- a reducing dopant having a work function of 2.9 eV or less a combination of two or more alkali metals is also preferable.
- a combination containing Cs for example, Cs and Na, Cs and K , Cs and Rb or a combination of Cs, Na and ⁇ It is preferable.
- an electron injection layer made of an insulator or a semiconductor may be further provided between the cathode and the organic layer.
- an insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkali earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides. . If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
- alkali metal chalcogenides include, for example, Li 0, LiO, Na
- alkaline earth metal chalcogenides include
- alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl.
- preferred alkaline earth metal halides include fluorides such as CaF, BaF, SrF, MgF and BeF, and halogens other than fluorides.
- the electron transport layer As a semiconductor constituting the electron transport layer, at least one element of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb, and Zn is used. One kind or a combination of two or more kinds of oxides, nitrides, oxynitrides and the like are included.
- the inorganic compound constituting the electron transport layer is preferably a microcrystalline or amorphous insulating thin film. If the electron transport layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such an inorganic compound include the above-mentioned alkali metal chalcogenides, alkaline earth metal lucogenides, alkali metal halides, and alkaline earth metal halides.
- a cathode As a cathode, a metal, an alloy, an electrically conductive compound and a low work function (4 eV or less) What uses these mixtures as an electrode material is used.
- electrode materials include sodium, sodium potassium alloy, magnesium, lithium, magnesium'silver alloy, aluminum / aluminum oxide, aluminum'lithium alloy, indium, rare earth metal, and the like.
- This cathode can be produced by forming these electrode materials by forming a thin film by a method such as vapor deposition or sputtering.
- the transmittance with respect to the light emitted from the cathode is greater than 10%.
- the sheet resistance as the cathode is preferably several hundred ⁇ / mouth or less.
- the film thickness is usually 5 nm to 1 ⁇ m, preferably 5 to 200 nm.
- the film thickness of the above material may be adjusted.
- organic EL applies an electric field to an ultra-thin film, pixel defects are likely to occur due to leaks and shorts. In order to prevent this, it is preferable to insert an insulating thin film layer between the pair of electrodes.
- Examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, cesium fluoride, cesium carbonate, Examples include aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide.
- an organic EL device by forming an anode, a light emitting layer, a hole injection layer as necessary, and an electron injection layer as necessary by the materials and methods exemplified above, and further forming a cathode. . It is also possible to fabricate organic EL elements from the cathode to the anode in the reverse order.
- a thin film made of an anode material on a suitable translucent substrate is 1 ⁇ m or less, preferably 10 to
- An anode is formed by a method such as vapor deposition or sputtering so that the film thickness is in the range of 200 nm.
- a hole injection layer made of the compound of the above formula (2) is provided on the anode.
- the hole injection layer can be formed by using a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. It is preferable to form by vacuum evaporation from the point of view.
- the deposition conditions vary depending on the compound used (the material of the hole injection layer), the crystal structure and recombination structure of the target hole injection layer, etc. deposition source temperature 50 to 450 ° C, vacuum degree of 10- 7 ⁇ ; 10- 3 torr, vapor deposition rate 0. 0;! ⁇ 50nm / sec, a substrate temperature of over 50 to 300 ° C, the thickness 5nm ⁇ 5 / im It is preferable to select appropriately within the range.
- a hole transport layer made of the compound of the formula (1) is formed on the hole injection layer.
- the formation method and conditions are the same as those for forming the hole injection layer.
- the light-emitting layer can also be formed by thinning the organic light-emitting material using a desired organic light-emitting material by a method such as vacuum deposition, sputtering, spin coating, or casting, but a homogeneous film can be obtained. It is preferable to form it by vacuum evaporation because it is easy and pinhole is not easily generated.
- the deposition conditions vary depending on the compound used, but can generally be selected from the same condition range as the hole transport layer.
- an electron transport layer is provided on the light emitting layer.
- the hole transport layer and light-emitting layer it is preferable to form the film by vacuum evaporation because it is necessary to obtain a homogeneous film.
- the vapor deposition conditions can be selected from the same condition ranges as those for the hole transport layer and the light emitting layer.
- a cathode can be stacked to obtain an organic EL device.
- the cathode is made of metal, and vapor deposition or sputtering can be used. In order to protect the underlying organic layer from damage during film formation, vacuum deposition is preferred.
- the organic EL devices described so far are preferably manufactured from the anode to the cathode in a single vacuum.
- the method for forming each layer of the organic EL device of the present invention is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used.
- the organic thin film layer containing the compound represented by the above formula (1) used in the organic EL device of the present invention can be prepared by vacuum evaporation, molecular beam evaporation (MBE), or solution dating in a solvent. Further, it can be formed by a known method using a coating method such as a spin coating method, a casting method, a bar coating method, or a roll coating method.
- each organic layer of the organic EL device of the present invention is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes occur, and conversely, if it is too thick, a high applied voltage is required. Usually, the range of several nm to 1 ⁇ m is preferable.
- the anode is set to + and the cathode is set to one polarity.
- Luminescence can be observed when a voltage of 5 to 40 V is applied. In addition, no current flows even when a voltage is applied with the opposite polarity, and no light emission occurs. In addition, when AC voltage is applied, uniform light emission is observed only when the anode is + and the cathode is of the same polarity.
- the AC waveform to be applied may be arbitrary.
- a glass substrate with 25 mm X 75 mm X l. 1 mm thick ITO transparent electrode (anode) (Zomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. Mount the glass substrate with the transparent electrode line after cleaning on the substrate holder of the vacuum evaporation system, and first cover the transparent electrode as a hole injection layer on the surface where the transparent electrode line is formed.
- a compound B-1 having a thickness of 60 nm and represented by the following formula was formed. Subsequent to the formation of the B-1 film, A-10 having a thickness of 20 nm and represented by the following formula was formed on the B-1 film as a hole transport layer.
- an anthracene derivative AN 1 and a styrylamine derivative D-1 represented by the following formula were formed at a film thickness ratio of 40: 2 on the A-10 film at a film thickness of 40 nm to form a blue light emitting layer.
- Alq shown in the following formula as an electron transport layer was formed by vapor deposition at a thickness of 20 nm. Filmed. Thereafter, LiF was deposited to a thickness of 1 nm as an electron injection layer.
- metal A1 was deposited by 150 nm to form a metal cathode to form an organic EL light emitting device.
- An organic EL device was produced in the same manner as in Example 1 except that Compound A-2 represented by the following formula was used instead of Compound A-10 as the hole transport layer in Example 1.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound A-6 represented by the following formula was used instead of Compound A-10 as the hole transport layer.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound A-9 represented by the following formula was used instead of Compound A-10 as the hole transport layer.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound A-11 represented by the following formula was used instead of Compound A-10 as the hole transport layer.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound A-15 represented by the following formula was used instead of Compound A-10 as the hole transport layer.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound A-25 represented by the following formula was used instead of Compound A-10 as the hole transport layer.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound A-26 represented by the following formula was used in place of Compound A-10 as the hole transport layer.
- Example 1 an organic EL device was produced in the same manner as in Example 1, except that Compound A-28 represented by the following formula was used instead of Compound A-10 as the hole transport layer.
- An organic EL device was produced in the same manner as in Example 1 except that Compound A-29 represented by the following formula was used in place of Compound A-10 as the hole transport layer in Example 1.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound B-5 represented by the following formula was used instead of Compound B-1 as the hole injection layer.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound B-7 represented by the following formula was used instead of Compound B-1 as the hole injection layer.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound B-8 represented by the following formula was used instead of Compound B-1 as the hole injection layer.
- An organic EL device was produced in the same manner as in Example 1 except that Compound B12 represented by the following formula was used instead of Compound B-1 as the hole injection layer in Example 1.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound B-25 represented by the following formula was used instead of Compound B-1 as the hole injection layer. [Chem 69]
- An organic EL device was produced in the same manner as in Example 1 except that Compound B-27 represented by the following formula was used instead of Compound B-1 as the hole injection layer in Example 1.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound B33 represented by the following formula was used instead of Compound B-1 as the hole injection layer.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound B39 represented by the following formula was used instead of Compound B-1 as the hole injection layer. [Chemical 72]
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that the compound (E-1) represented by the following formula was used in place of Compound A-10 as the hole transport layer.
- Example 1 E-2 shown in the following formula was used instead of Compound B-1 as the hole injection layer, and Compound B-1 was used instead of Compound A-10 as the hole transport layer.
- An organic EL device was fabricated in the same manner as in Example 1.
- Comparative Example 3 An organic EL device was produced in the same manner as in Example 1 except that Compound E-2 was used in place of Compound B-1 as the hole injection layer in Example 1.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that the compound (E-3) represented by the following formula was used instead of the compound B-1 as the hole injection layer.
- Example 1 an organic EL light emitting device was formed in the same manner as in Example 1 except that the thickness of the hole injection layer made of Compound B-1 was 80 nm and the hole transport layer was not formed.
- Comparative Example 5 an organic EL device was produced in the same manner as in Comparative Example 5, except that Compound A-10 was used instead of Compound B-1 as the hole injection layer.
- Comparative Example 5 an organic EL device was produced in the same manner as in Comparative Example 5, except that Compound B-39 was used instead of Compound B-1 as the hole injection layer.
- Table 1 shows the device performance results of Examples;! To 18 and Comparative Examples 1 to 7.
- a 1 mm thick glass substrate with ITO transparent electrode (anode) (Zomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes.
- a glass substrate with a transparent electrode line after cleaning is mounted on a substrate holder of a vacuum evaporation apparatus, and a film is first formed on the surface where the transparent electrode line is formed so as to cover the transparent electrode as a hole injection layer.
- An acceptor compound C 1 having a thickness of lOnm and having the following formula was formed.
- B 1 having a thickness of 50 nm was formed as a hole transport layer (1) on the C-1 film.
- an A-10 film having a thickness of 20 nm was formed as a hole transport layer (2) on the B-1 film.
- AN-1 and D-1 were deposited at a film thickness ratio of 40: 2 at a film thickness of 40 nm to form a blue light emitting layer.
- Alq was deposited as an electron transport layer with a thickness of 20 nm by vapor deposition. Thereafter, LiF was deposited to a thickness of 1 nm as an electron injection layer. On this LiF film, 150 nm of metal A1 was deposited to form a metal cathode to form an organic EL light emitting device.
- Example 19 an organic EL device was produced in the same manner as in Example 19 except that the compound C 2 represented by the following formula was used instead of the compound C 1 as the hole injection layer.
- An organic EL device was produced in the same manner as in Example 19 except that Compound A-2 was used instead of Compound A-10 as the hole transport layer (2) in Example 19.
- Example 23 An organic EL device was produced in the same manner as in Example 19 except that Compound A-6 was used in place of Compound A-10 as the hole transport layer (2) in Example 19. [0223] Example 23
- An organic EL device was produced in the same manner as in Example 19 except that Compound A-9 was used instead of Compound A-10 as the hole transport layer (2) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound A-11 was used in place of Compound A-10 as the hole transport layer (2) in Example 19.
- Example 19 an organic EL device was produced in the same manner as in Example 19 except that Compound A-15 was used instead of Compound A-10 as the hole transport layer (2).
- An organic EL device was produced in the same manner as in Example 19 except that Compound A-25 was used instead of Compound A-10 as the hole transport layer (2) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound A-26 was used instead of Compound A-10 as the hole transport layer (2) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound A- 28 was used instead of Compound A-10 as the hole transport layer (2) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound A-29 was used instead of Compound A-10 as the hole transport layer (2) in Example 19.
- Example 19 an organic EL device was produced in the same manner as in Example 19 except that compound (B-2) of the following formula was used instead of compound B-1 as the hole transport layer (1). .
- An organic EL device was produced in the same manner as in Example 19 except that Compound B-5 was used instead of Compound B-1 as the hole transport layer (1) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound B-7 was used instead of Compound B-1 as the hole transport layer (1) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound B-8 was used instead of Compound B-1 as the hole transport layer (1) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound B-12 was used instead of Compound B-1 as the hole transport layer (1) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound B-25 was used instead of Compound B-1 as the hole transport layer (1) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound B-33 was used instead of Compound B-1 as the hole transport layer (1) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound B-39 was used instead of Compound B-1 as the hole transport layer (1) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound E-2 was used instead of Compound B-1 as the hole transport layer (1) in Example 19.
- An organic EL device was produced in the same manner as in Example 19 except that Compound E-3 was used instead of Compound B-1 as the hole transport layer (1) in Example 19.
- Example 19 Comparative Example 10 In Example 19, except that Compound E-3 was used instead of Compound B-1 as the hole transport layer (1) and B-1 was used instead of A-10 as the hole transport layer (2). An organic EL device was fabricated in the same manner as in Example 19.
- a glass substrate with 25 mm X 75 mm X l. 1 mm thick ITO transparent electrode (anode) (Zomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. Mount the glass substrate with the transparent electrode line after cleaning on the substrate holder of the vacuum evaporation system, and first cover the transparent electrode as a hole injection layer on the surface where the transparent electrode line is formed. An acceptor compound C 1 having a film thickness of 60 nm was formed. Following the formation of the C-1 film, an A-10 film having a thickness of 20 nm was formed as a hole transport layer on the C-1 film.
- AN-1 and D-1 were deposited at a film thickness ratio of 40: 2 at a film thickness of 40 nm to form a blue light emitting layer.
- Alq was deposited as an electron transport layer with a thickness of 20 nm by vapor deposition. Thereafter, LiF was deposited to a thickness of 1 nm as an electron injection layer. On this LiF film, 150 nm of metal A1 was deposited to form a metal cathode to form an organic EL light emitting device.
- An organic EL device was produced in the same manner as in Comparative Example 11 except that Compound B-1 was used instead of Compound A-10 in Comparative Example 11 instead of Compound A-10.
- An organic EL device was produced in the same manner as in Comparative Example 11 except that Compound B-39 was used instead of Compound A-10 as the hole transport layer in Comparative Example 11.
- Table 2 shows the device performance results of Examples 19 to 37 and Comparative Examples 8 to 13;
- Example 19 C-1 B-1 A- 10 6.4 8.2 Blue 8000
- Example 20 C-2 B 1 A-10 6.4 8.2 Blue 8000
- Example 21 C-1 B-1 A-2 6.6 8.3 Blue 7000
- Example 22 C-1 B-1 A- 6 6.5 8.3 7000
- Example 23 C-1 B-1 A-9 6.4 8, 3 Blue 8000
- Example 24 C-1 B 1 A-11 6.4 8.2 Blue 8000
- Example 25 C- 1 B-1 A-15 6.4 8.3 Blue 8000
- Example 26 C- 1 B-1 A-25 6.6 8.3 Blue 8000
- Example 27 C-1 B-1 A-26 6.5 8.2 Blue 8000
- Example 30 C-1 B-2 A-10 6.4 8.3 Blue 8000
- Example 31 C-1 B-5 A -10 6.4 8.3 Blue 8000
- Example 32 C-1 B-7 A-10 6.4 8, 3 Blue 8000
- the element structure of the organic EL element of the present invention has a structure in which holes are likely to flow specifically by using a specific material system, and the number of holes injected into the light emitting layer is remarkably increased. .
- the electron can be prevented from reaching the hole transport layer, thereby extending the life.
- the high efficiency characteristic peculiar to A-10 is maintained, and further low voltage and long life can be realized.
- the above-described tendency is considered to be the same even when each peripheral compound is used. Further, the same tendency can be obtained by using an acceptor material at the anode interface. By using an acceptor material, we were able to achieve even lower voltage.
- the organic EL device of the present invention can be used as a material for various colors of organic EL including blue, and can be applied to various display devices, displays, backlights, illumination light sources, signs, signs, interiors, and the like. Particularly, it is suitable as a display element for a color display.
Description
Claims
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KR1020087030995A KR101422864B1 (ko) | 2006-06-22 | 2007-06-19 | 복소환 함유 아릴아민 유도체를 이용한 유기 전계발광 소자 |
CN200780022945.1A CN101473464B (zh) | 2006-06-22 | 2007-06-19 | 应用含有杂环的芳胺衍生物的有机电致发光元件 |
JP2008522454A JP5616582B2 (ja) | 2006-06-22 | 2007-06-19 | 複素環含有アリールアミン誘導体を用いた有機エレクトロルミネッセンス素子 |
EP07767148.5A EP2031670B1 (en) | 2006-06-22 | 2007-06-19 | Organic electroluminescent device employing heterocycle-containing arylamine derivative |
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US9960360B2 (en) | 2018-05-01 |
US11678571B2 (en) | 2023-06-13 |
EP2031670A4 (en) | 2011-05-04 |
US20180090685A1 (en) | 2018-03-29 |
KR20090021174A (ko) | 2009-02-27 |
US20160020403A1 (en) | 2016-01-21 |
US20080014464A1 (en) | 2008-01-17 |
CN101473464B (zh) | 2014-04-23 |
US10283717B2 (en) | 2019-05-07 |
KR101422864B1 (ko) | 2014-07-24 |
TW200816538A (en) | 2008-04-01 |
JPWO2007148660A1 (ja) | 2009-11-19 |
US11094888B2 (en) | 2021-08-17 |
US11152574B2 (en) | 2021-10-19 |
US20210376247A1 (en) | 2021-12-02 |
US10263192B2 (en) | 2019-04-16 |
JP5616582B2 (ja) | 2014-10-29 |
EP2031670B1 (en) | 2013-11-27 |
CN101473464A (zh) | 2009-07-01 |
EP2031670A1 (en) | 2009-03-04 |
US20180040828A1 (en) | 2018-02-08 |
TWI478410B (zh) | 2015-03-21 |
US20210083194A1 (en) | 2021-03-18 |
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