Deuterated semi-conducting organic compounds used for opto-electronic devices

• US 20030138657A1
• Filed: 01/22/2003
• Published: 07/24/2003
• Est. Priority Date: 12/07/2000
• Status: Active Grant

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Li, Xiao-Chang Charles, Ueno, Kazunori
• Granted Patent: US 6,686,067 B2
• Time in Patent Office: Days
• US Class Current: 428/621
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/113 Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/114 Poly-phenylenevinylene; Derivatives thereof
• CPC Class Codes: H10K 85/115 Polyfluorene; Derivatives thereof
• CPC Class Codes: H10K 85/141 comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
• CPC Class Codes: H10K 85/30 Coordination compounds
• CPC Class Codes: H10K 85/311 Phthalocyanine
• CPC Class Codes: H10K 85/322 comprising boron
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/331 Metal complexes comprising an iron-series metal, e.g. Fe, Co, Ni
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/351 Metal complexes comprising lanthanides or actinides, e.g. comprising europium
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• 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 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: Y10S 428/917 Electroluminescent
• CPC Class Codes: Y10T 428/12535 with additional, spatially distinct nonmetal component

Abstract

Organic semiconductors consisting of conjugated chromophores wherein one or more hydrogen atoms are deuterated are disclosed. Methods of preparing such organic semiconductors are described. The organic semiconducting compounds exhibit remarkably high luminescence and good thermal stability. Applications of these materials for optoelectronic devices, such as light-emitting devices and photodiodes, with enhanced performance and lifetime are disclosed. The disclosed materials can be used as emissive layer, charge-transporting layer, or energy transfer (i.e. phosphorescence dopant) material in organic light-emitting devices.

Claims

1. An organic semiconductor comprising a conjugated chromophore selected from a linear conjugated organic compound or a polymer, a cyclic ring, a fused cyclic ring, a heterocyclic ring, a fused heterocyclic ring, a chelate or oraganometalic material having the formula C_AM_B, where C denotes a conjugated chromophore, M denotes a metal selected from, Li, Na, K, Be, Mg, Ca, Ti, Cr, Mo, Mn, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Zn, Cd, B, Al, Ga, In, Si, N, P, and A and B denote a number from 1 to 10, respectively, and combinations thereof, said chromophore having with at least 5 conjugated bonds wherein protons linked to the conjugated bonds are partially or fully deuterated.

2. An organic semiconductor according to claim 1, wherein the conjugated chromophore is partially deuterated, and wherein un-deuterated sites are chemically bound to a moiety selected from hydrogen atoms, halogen atoms, alkyl, alkoxyl, thiol, silyl, aromatic rings, or heteroaromatic rings.

3. An organic semiconductor according to claim 1, wherein the organic semiconductor is luminescent.

4. An organic semiconductor according to claim 1, wherein the organic semiconductor possesses charge injection, hole blocking, or exciton blocking properties.

5. An organic semiconductor according to claim 1, wherein the organic semiconductor promotes energy transfer.

6. An organic semiconductor according to claim 1, wherein the organic semiconductor produces greater than 25% singlet excitons for light emission.

26. An organic semiconductor according to claim 1, fabricated as an organic luminescent device.

30. An organic luminescent device comprising:

a first electrode surface;

a first thin film of conjugated luminescent polymer comprising an organic semiconductor according to claim 1, wherein the luminescent polymer is electrically coupled to the first electrode surface; and

a second electrode, electrically coupled to the conjugated luminescent polymer.

7. An organic semiconductor comprising a conjugated chromophore with a linear conjugated organic compound or a polymer with at least 5 conjugated bonds, wherein protons linked to the conjugated bonds are partially or fully deuterated.

8. An organic semiconductor according to claim 7, wherein the conjugated chromophore is partially deuterated, and wherein un-deuterated sites are chemically bound to a moiety selected from hydrogen atoms, halogen atoms, alkyl, alkoxyl, thiol, silyl, aromatic rings, or heteroaromatic rings.

9. An organic semiconductor according to claim 7, wherein the organic semiconductor is luminescent.

10. An organic semiconductor according to claim 7, wherein the organic semiconductor possesses charge injection, hole blocking, or exciton blocking properties.

11. An organic semiconductor according to claim 7, wherein the organic semiconductor promotes energy transfer.

12. An organic semiconductor according to claim 7, wherein the organic semiconductor produces greater than 25% singlet excitons for light emission.

27. An organic semiconductor according to claim 7, fabricated as an organic luminescent device.

13. An organic semiconductor comprising a conjugated chromophore with a cyclic ring, a fused cyclic ring, or a combination thereof, in the form of a conjugated organic compound or a polymer with at least 5 conjugated bonds, wherein protons linked to the conjugated bonds are partially or fully deuterated.

14. An organic semiconductor according to claim 13, wherein the conjugated chromophore is partially deuterated, and wherein un-deuterated sites are chemically bound to a moiety selected from hydrogen atoms, halogen atoms, alkyl, alkoxyl, thiol, silyl, aromatic rings, or heteroaromatic rings.

15. An organic semiconductor according to claim 13, wherein the organic semiconductor is luminescent.

16. An organic semiconductor according to claim 13, wherein the organic semiconductor possesses charge injection, hole blocking, or exciton blocking properties.

17. An organic semiconductor according to claim 13, wherein the organic semiconductor promotes energy transfer.

18. An organic semiconductor according to claim 13, wherein the organic semiconductor produces greater than 25% singlet excitons for light emission.

28. An organic semiconductor according to claim 13, fabricated as an organic luminescent device.

19. An organic semiconductor of the formula C_AM_B, where C denotes a conjugated chromophore, wherein protons linked to the conjugated bonds are partially or fully deuterated;

M denotes a metal selected from, Li, Na, K, Be, Mg, Ca, Ti, Cr, Mo, Mn, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Zn, Cd, B, Al, Ga, In, Si, N, and P;

A and B denote a number from 1 to 10, respectively.

20. An organic semiconductor according to claim 19, wherein A and B denote a number from 1 to 4, respectively.

21. An organic semiconductor according to claim 19, wherein the conjugated chromophore is partially deuterated, and wherein un-deuterated sites are chemically bound to a moiety selected from hydrogen atoms, halogen atoms, alkyl, alkoxyl, thiol, silyl, aromatic rings, or heteroaromatic rings.

22. An organic semiconductor according to claim 19, wherein the organic semiconductor is luminescent.

23. An organic semiconductor according to claim 19, wherein the organic semiconductor possesses charge injection, hole blocking, or exciton blocking properties.

24. An organic semiconductor according to claim 19, wherein the organic semiconductor promotes energy transfer.

25. An organic semiconductor according to claim 19, wherein the organic semiconductor produces greater than 25% singlet excitons for light emission.

29. An organic semiconductor according to claim 19, fabricated as an organic luminescent device.