Amorphous organic thin film element and amorphous organic polymer composition

• US 5,536,588 A
• Filed: 07/27/1993
• Issued: 07/16/1996
• Est. Priority Date: 08/27/1992
• Status: Expired due to Fees

• Current Assignee: Kabushiki Kaisha Toshiba (Toshiba Corporation)
• Original Assignee: Kabushiki Kaisha Toshiba (Toshiba Corporation)
• Inventors: Naito, Katsuyuki
• Primary Examiner(s): Nold, Charles R.
• Application Number:
  US08/097,029
• Time in Patent Office: 1,085 Days
• Field of Search: 428/917, 428/690, 313/503-509
• US Class Current: 428/690
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: G03G 5/06 characterised by the photoconductive material being organic
• CPC Class Codes: G03G 5/0661 in different ring systems, each system containing at least one hetero ring
• 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: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 85/60 Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• 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 85/6565 Oxadiazole compounds
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Disclosed is an amorphous organic thin-film element containing dye molecules with ΣΔStr,m (J/(K.kmol))/Mw of 60 or less, assuming that the molecular weight is Mw and the sum total of an entropy change of melting and entropy changes of transition from a glass transition point to a melting point is ΣΔStr,m (J/(K.kmol)), and having a high heat resistance and a high stability over long periods of time.

Claims

1. An amorphous organic thin-film element comprising an organic thin film containing dye molecules with Σ

Δ

Str,m (J/(K.kmol))/Mw of not more than 60, assuming that a molecular weight is Mw and the sum total of an entropy change of melting and entropy changes of transition from a glass transition point to a melting point is Σ

Δ

Str,m (J/(K.kmol)).

2. An element according to claim 1, wherein the Σ

Δ

Str,m (J/(K.kmol))/Mw of said dye molecule is not more than 55.

3. An element according to claim 1, wherein the glass transition point of said dye molecule is not less than 170°

C.

4. An element according to claim 1, wherein Mw/(Tm.Δ

Hm) of said dye molecule is not less than 0.04, assuming that a molecular weight is Mw, a melting point is Tm (K), and an enthalpy change of melting is Δ

Hm (kJ/mol).

5. An element according to claim 1, wherein said dye molecule has a symmetrical structure.

6. An element according to claim 1, wherein said dye molecule has a phenyl group, a polyphenyl group, or a condensed ring at the center thereof, and dye skeletons are radially bonded to the skeleton of said group.

7. An element according to claim 6, wherein a bulky substituent group is bonded to the outermost portion of said dye molecule.

8. An element according to claim 7, wherein said bulky substituent group is a t-butyl group.

9. An element according to claim 1, wherein any of a hole-transport layer, a luminescent layer, and an electron-transport layer, which constitute a three-layered structure of said organic thin film, contains dye molecules with Σ

Δ

Str,m (J/K.kmol))/Mw of not more than 60 and emits light upon application of an electric field.

14. An element according to claim 6 wherein at least three dye skeleton molecules are bonded to the central skeletal structure of the dye molecule.

15. An element according to claim 6 wherein the central skeletal structure of the dye molecule consists of a benzene ring, and dye skeletons are introduced at the 1-, 3-, and 5-positions of the benezene ring.

16. An element according to claim 6 wherein the central skeletal structure of the dye molecule consists of a biphenyl ring, and dye skeletons are introduced at the 3-, 3'"'"'-, 5-, and 5'"'"'-positions of the biphenyl ring.

10. An amorphous organic thin-film element comprising an organic thin film containing dye molecules which have a molecular weight of not less than 350, and each of which has a plurality of sites where an intermolecular hydrogen bond can be formed.

11. An element according to claim 10, wherein the molecular weight of said dye molecule is not less than 450.

12. An element according to claim 10, wherein said dye molecules have Σ

Δ

Str,m (J/(K.kmol))/Mw of not more than 60, assuming that a molecular weight is Mw and the sum total of an entropy change of melting and entropy changes of transition from a glass transition point to a melting point is Σ

Δ

Str,m (J/(K.kmol)).

13. An amorphous organic thin-film element comprising, in an amorphous polymer, dye molecules with Σ

Δ

Str,m (J/(K.kmol))/Mw of not more than 60, assuming that a molecular weight is Mw and the sum total of an entropy change of melting and entropy changes of transition from a glass transition point to a melting point is Σ

Δ

Str,m (J/(K.kmol)).