Organic electroluminescence device
Object To provide an organic electroluminescence device including, in order to improve the device characteristics of the organic electroluminescence device, particularly, to absorb light having the wavelengths of from 400 nm to 410 nm from sunlight, not to affect a material inside the device, and to significantly improve the light extraction efficiency, a capping layer formed of a material that has a high absorption coefficient, a high refractive index, and an excellent stability, durability, and light resistance of a thin film, and does not absorb light in the blue, green, and red wavelength range. Solving Means An organic electroluminescence device including at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode, and a capping layer in the stated order, in which the capping layer includes a material having an extinction coefficient of not less than 0.3 at wavelengths of from 400 nm to 410 nm and an absorbance of not less than 0.2 at wavelengths of from 400 nm to 410 nm in an absorption spectrum of a concentration of 10 −5 mol/l.
1. An organic electroluminescence device comprising: at least
an anode electrode;
a hole transport layer;
a light emitting layer;
an electron transport layer;
a cathode electrode; and
a capping layer in the stated order,
wherein the capping layer includes a material having an extinction coefficient of not less than 0.3 at wavelengths of from 400 nm to 410 nm and an absorbance of not less than 0.2 at wavelengths of from 400 nm to 410 nm in the absorption spectrum of a concentration of 10 −5 mol/l,
wherein the capping layer includes an arylamine compound represented by a following general formula (1):
where, in the general formula (1), Ar 1 , Ar 2 , Ar 3 , and Ar 4 may be the same or different from each other and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, n represents an integer of 0 to 4, wherein at least one of Ar 1 , Ar 2 , Ar 3 , and Ar 4 is a monovalent group represented by a following structural formula (B) or has the monovalent group as a substituent;
where, in the structural formula (B), R 1 , R 2 , R 3 , and R 4 may be the same or different from each other, be a linking group, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms, which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms, which may have a substituent, a linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 1 , R 2 , R 3 , and R 4 may be bonded to each other to form a ring via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or N—Ar 8 , where Ar 8 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, X represents a carbon atom or a nitrogen atom, Y represents a carbon atom, an oxygen atom, a sulfur atom, or a nitrogen atom, Ar 5 represents a linking group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, wherein Ar 6 and Ar 7 may be the same or different from each other, be a linking group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, wherein Y does not have Ar 7 in the case that Y is an oxygen atom or a sulfur atom, wherein any one of Ar 5 , Ar 6 , and Ar 7 is a linking group or a substituent in the case that X and Y are each a nitrogen atom, wherein X does not have Ar 6 in the case that X is a nitrogen atom and Y is a carbon atom, wherein Ar 8 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, wherein only one of R 1 , R 2 , R 3 , R 4 , Ar 5 , Ar 6 , and Ar 7 is a linking group, and a case that X is a nitrogen atom and Y is an oxygen atom or sulfur atom is excluded; and
wherein the electron transport layer includes a following compound (3-4):
2. The organic electroluminescence device according to claim 1 , wherein
the material of the capping layer has an extinction coefficient of not less than 0.1 at wavelengths of from 410 nm to 430 nm.
3. The organic electroluminescence device according to claim 1 , wherein
the structural formula (B) is a monovalent group represented by a following structural formula (B-1):
where, in the structural formula (B-1), R 1 , R 2 , R 3 , and R 4 may be the same or different from each other, be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms, which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms, which may have a substituent, a linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 1 , R 2 , R 3 , and R 4 may be bonded to each other to form a ring via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or N—Ar 8 , wherein Ar 8 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
4. The organic electroluminescence device according to claim 1 , wherein
the structural formula (B) is a monovalent group represented by a following structural formula (B-2):
where, in the structural formula (B-2), R 1 , R 3 , and R 4 may be the same or different from each other, be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms, which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms, which may have a substituent, a linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 3 and R 4 may be bonded to each other to form a ring via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or N—Ar 8 , wherein Ar 6 and Ar 8 may be the same or different from each other and each represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
5. The organic electroluminescence device according to claim 1 , wherein
the structural formula (B) is a monovalent group represented by a following structural formula (B-3):
where, in the structural formula (B-3), R 1 , R 2 , R 3 , and R 4 may be the same or different from each other, be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms, which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms, which may have a substituent, a linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 1 , R 2 , R 3 , and R 4 may be bonded to each other to form a ring via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or N—Ar 8 , wherein Ar 8 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
6. The organic electroluminescence device according to claim 1 , wherein
the structural formula (B) is a monovalent group represented by a following structural formula (B-4):
where, in the structural formula (B-4), R 1 , R 2 , R 3 , and R 4 may be the same or different from each other, be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms, which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms, which may have a substituent, a linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 1 , R 2 , R 3 , and R 4 may be bonded to each other to form a ring via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or N—Ar 8 , wherein Ar 8 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
7. The organic electroluminescence device according to claim 1 , wherein
the structural formula (B) is a monovalent group represented by a following structural formula (B′):
where, in the structural formula (B′), R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 may be the same or different from each other, be a linking group, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms, which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms, which may have a substituent, a linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 may be bonded to each other to form a ring via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or N—Ar 8 , where X represents a carbon atom or a nitrogen atom, Y represents a carbon atom, an oxygen atom, a sulfur atom, or a nitrogen atom, wherein Ar 5 represents a linking group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, wherein Ar 6 and Ar 7 may be the same or different from each other and each represent a linking group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, wherein Y does not have Ar 7 in the case that Y is an oxygen atom or a sulfur atom, wherein any one of Ar 5 , Ar 6 , and Ar 7 is a linking group or a substituent in the case that X and Y are each a nitrogen atom, wherein X does not have Ar 6 in the case that X is a nitrogen atom and Y is a carbon atom, wherein Ar 8 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, wherein only one of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Ar 5 , Ar 6 , and Ar 7 is a linking group, and a case that X is a nitrogen atom and Y is an oxygen atom or sulfur atom is excluded.
8. The organic electroluminescence device according to claim 1 , wherein
n is 0 in the general formula (1).
9. The organic electroluminescence device according to claim 1 , wherein
n is 1 in the general formula (1).
10. The organic electroluminescence device according to claim 1 , wherein
n is 2 in the general formula (1).
11. The organic electroluminescence device according to claim 1 , wherein
any two of Ar 1 , Ar 2 , Ar 3 , and Ar 4 are each a monovalent group represented by the structural formula (B) or each has the monovalent group as a substituent in the general formula (1).
12. The organic electroluminescence device according to claim 1 , wherein
Ar 1 and Ar 4 are each a monovalent group represented by the structural formula (B) or each has the monovalent group as a substituent in the general formula (1).
13. The organic electroluminescence device according to claim 1 , wherein
the capping layer has a thickness in the range of 30 nm to 120 nm.
14. The organic electroluminescence device according to claim 1 , wherein
the capping layer has a refractive index of not less than 1.85 in the wavelength range of 400 nm to 750 nm of light transmitted through the capping layer.
15. A method of using a compound represented by the general formula (1) as a capping layer of an organic electroluminescence device.