Electronic device, organic electroluminescent element, organic thin-film solar cell, and dye-sensitized solar cell

• US 9,991,453 B2
• Filed: 05/21/2014
• Issued: 06/05/2018
• Est. Priority Date: 05/22/2013
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Konica Minolta Inc.
• Inventors: Kita, Hiroshi, Tanaka, Tatsuo, Katakura, Rie
• Primary Examiner(s): Hammer, Katie L
• Application Number:
  US14/888,295
• Publication Number:
  US 20160079548A1
• Time in Patent Office: 1,476 Days
• Field of Search: None
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1074 containing more than three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H01B 1/12 organic substances organic macromolecular compounds or compositions C08
• CPC Class Codes: H01G 9/2031 comprising titanium oxide, e.g. TiO2 H01G9/2036 takes precedence
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H05B 33/20 characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 30/151 the wide bandgap semiconductor comprising titanium oxide, e.g. TiO2
• CPC Class Codes: H10K 30/30 comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 85/113 : Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/151 : Copolymers
• CPC Class Codes: H10K 85/215 : comprising substituents, e.g. PCBM
• CPC Class Codes: H10K 85/324 : comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/341 : Transition metal complexes, e.g. Ru(II)polypyridine complexes H10K85/331 takes precedence
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/615 : Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/622 : containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/631 : Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/633 : comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 : comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 : comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
• CPC Class Codes: Y02E 10/542 : Dye sensitized solar cells
• CPC Class Codes: Y02E 10/549 : Organic PV cells

Abstract

This invention addresses the problem of providing an electronic device, organic electroluminescent device, conductive film, organic thin-film solar cell, and dye-sensitized solar cell provided with a charge-transporting thin film that exhibits excellent stability. In the presence of external disturbances, the charge-transporting thin film exhibits little in the way of fluctuations, and the resistance of the charge-transporting thin film changes little over time as current is supplied. As one of the secondary effects thereof, the charge-transporting thin film results in little in the way of changes in emission characteristics over time. This electronic device, which is provided with a charge-transporting thin film that contains one or more functional organic compounds having chiral elements, is characterized by the provision of a charge-transporting thin film wherein the total of the number of chiral elements per molecule in each type of the functional organic compounds summed over all types of the functional organic compounds is four or more.

Claims

1. An electronic device comprising a charge-transporting thin film containing at least two types of functional organic compounds having chiral elements,

wherein the total number of chiral elements per molecule in each type of the functional organic compounds, summed over all the functional organic compounds, is four or more,

at least one of the functional organic compounds is a metal complex,

the metal complex has two or more chiral elements per molecule, and thereby comprises a mixture of enantiomers and diastereomers, and

at least one of the functional organic compounds is a host compound and comprises a mixture of enantiomers and diastereomers.

2. The electronic device according to claim 1, wherein the total number of chiral elements per molecule, summed over all the functional organic compounds, is within a range of five to fifteen.

3. The electronic device according to claim 1, wherein each of the at least two types of the functional organic compounds, which are other than the metal complex and the host compound, comprises at least one selected from a mixture of enantiomers and a mixture of diastereomers.

4. The electronic device according to claim 1, wherein all of the at least two types of the functional organic compounds comprise a mixture of enantiomers and diastereomers.

5. The electronic device according to claim 1, wherein at least one of the functional organic compounds having chiral elements have a biaryl structure which has chiral elements due to hindered rotation between two aryl moieties, such that the at least one of the functional organic compounds comprises a mixture of atropisomers.

6. The electronic device according to claim 1, wherein the at least one type of the functional organic compounds having chiral elements is a compound which emits light during excitation under an electric field.

7. The electronic device according to claim 6, wherein the compound which emits light during excitation under an electric field is the metal complex.

8. An electroluminescent element which is the electronic device according to claim 1.

9. An electrically conductive film which is the electronic device according to claim 1.

10. An organic thin-film solar cell which is the electronic device according to claim 1.

11. A dye-sensitized solar cell which is the electronic device according to claim 1.

12. The electronic device according to claim 1, wherein all of the at least two types of the functional organic compounds having chiral elements have a biaryl structure which has chiral elements due to hindered rotation between two aryl moieties, such that all of the at least two types of the functional organic compounds comprise a mixture of atropisomers.

14. The electronic device according to claim 1, wherein the charge-transporting thin film contains the functional organic compounds having chiral elements;

and

the thin film further comprises a volatile organic material having a boiling point lower than 300°

C. under normal pressure, wherein the volatile organic material has an asymmetric carbon atom.

15. The electronic device according to claim 10, wherein the volatile organic material comprises at least one selected from the group consisting of a substituted aliphatic hydrocarbon solvent having an asymmetric carbon atom, a substituted aromatic hydrocarbon solvent having an asymmetric carbon atom, and a substituted halogen solvent having an asymmetric carbon atom.

16. The electronic device according to claim 10, wherein the volatile organic material comprises at least one selected from the group consisting of 2-ethylhexane, sec-butyl ether, 2-pentanol, 2-methyltetrahydrofuran, 2-propylene glycol monomethyl ether, 2,3-dimethyl-1,4-dioxane, sec-butylbenzene, 4-(sec-butyl)biphenyl, and 2-methylcyclohexylbenzene.

13. An electronic device comprising a charge-transporting thin film containing one or more types of functional organic compounds having chiral elements,

wherein the total number of chiral elements per molecule in each type of the functional organic compounds, summed over all the functional organic compounds, is four or more,

the charge-transporting thin film contains the functional organic compounds having chiral elements;

and

the thin film further comprises a volatile organic material having a boiling point lower than 300°

C. under normal pressure, wherein the volatile organic material has an asymmetric carbon atom.