Organic semiconductor element

• US 7,420,203 B2
• Filed: 02/18/2005
• Issued: 09/02/2008
• Est. Priority Date: 12/05/2001
• Status: Expired due to Term

• Current Assignee: Semiconductor Energy Laboratory Co., Ltd.
• Original Assignee: Semiconductor Energy Laboratory Co., Ltd.
• Inventors: Seo, Satoshi, Yamazaki, Hiroko, Tsutsui, Tetsuo
• Primary Examiner(s): Sefer; A.
• Assistant Examiner(s): Wilson; Scott R
• Application Number:
  US11/061,500
• Publication Number:
  US 20050156197A1
• Time in Patent Office: 1,292 Days
• Field of Search: None
• US Class Current: 257/40
• CPC Class Codes: B82Y 10/00 Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
• CPC Class Codes: H10K 10/701 Organic molecular electronic devices
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 30/20 comprising organic-organic junctions, e.g. donor-acceptor junctions
• CPC Class Codes: H10K 30/211 comprising multiple junctions, e.g. double heterojunctions
• CPC Class Codes: H10K 30/57 comprising multiple junctions, e.g. tandem PV cells
• CPC Class Codes: H10K 39/00 Integrated devices, or assemblies of multiple devices, comprising at least one organic radiation-sensitive element covered by group H10K30/00
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/125 specially adapted for multicolour light emission, e.g. for emitting white light
• CPC Class Codes: H10K 50/13 comprising stacked EL layers within one EL unit
• CPC Class Codes: H10K 50/155 comprising dopants
• CPC Class Codes: H10K 50/165 comprising dopants
• CPC Class Codes: H10K 50/19 Tandem OLEDs
• CPC Class Codes: H10K 59/32 Stacked devices having two or more layers, each emitting at different wavelengths
• CPC Class Codes: H10K 85/30 Coordination compounds
• CPC Class Codes: H10K 85/311 Phthalocyanine
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/60 Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/611 Charge transfer complexes
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/621 : Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
• 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 85/649 : Aromatic compounds comprising a hetero atom
• CPC Class Codes: H10K 85/6565 : Oxadiazole compounds
• CPC Class Codes: Y02E 10/50 : Photovoltaic [PV] energy
• CPC Class Codes: Y02E 10/549 : Organic PV cells
• CPC Class Codes: Y02P 70/50 : Manufacturing or production processes characterised by the final manufactured product

Abstract

By introducing new concepts into a structure of a conventional organic semiconductor element and without using a conventional ultra thin film, an organic semiconductor element is provided which is more reliable and has higher yield. Further, efficiency is improved particularly in a photoelectronic device using an organic semiconductor. Between an anode and a cathode, there is provided an organic structure including alternately laminated organic thin film layer (functional organic thin film layer) realizing various functions by making an SCLC flow, and a conductive thin film layer (ohmic conductive thin film layer) imbued with a dark conductivity by doping it with an acceptor and a donor, or by the like method.

Claims

1. An electronic device comprising:

a cathode;

an anode;

a structure comprising a first through an n-th functional thin film layers (where n is an integer equal to or greater than

     2) between the cathode and the anode,

a conductive thin film layer between a k-th functional thin film layer (where k is an integer of 1≦

k≦

(n−

1)) and a (k+1)th functional thin film layer,

wherein the conductive thin film layer contacts with the k-th functional thin film layer and the (k+1)th functional thin film layer,

wherein the conductive thin film layer comprises a first layer and a second layer,

wherein the first layer includes an acceptor, and

wherein each of the functional thin film layers comprises a light emitting layer.

2. The electronic device according to claim 1, wherein the first layer is n-type organic semiconductor.

3. The electronic device according to claim 1, wherein the second layer is p-type organic semiconductor.

4. The electronic device according to claim 1 wherein the fist layer comprises a material selected from the group consisting of F₁₆—

CuPc, 3,4,9,10-perylene tetracarboxylic acid derivatives, PV, Me-PTC, PTCDA, naphthalenecarboxylic anhydrides, naphthalenecarboxylic diimide, TCNQ, TCE, benzoquinone, 2,6-naphthoquinone, DDQ, p-fluoranil, tetrachlorodiphenoquinone, nickelbisdiphenylglyoxime, BCP, and PBD.

5. The electronic device according to claim 1, wherein the second layer comprises a material selected from the group consisting of CuPc, phthalocyanine bound to a metal, phthalocyanine bound to no metals, TTF, TTT, methylphenothiazine, N-isopropylcarbazole, TPD, and CBP.

6. An electronic device comprising:

a cathode;

an anode;

a structure comprising a first through an n-th functional thin film layers (where n is an integer equal to or greater than

     2) between the cathode and the anode,

a conductive thin film layer between a k-th functional thin film layer (where k is an integer of 1≦

k≦

(n−

1)) and a (k+1)th functional thin film layer,

wherein the conductive thin film layer contacts with the k-th functional thin film layer and the (k+1)th functional thin film layer,

wherein the conductive thin film layer comprises a first layer including a donor and a second layer including an acceptor,

wherein the first layer is disposed closer to the anode than the second layer, and

wherein each of the functional thin film layers comprises a light emitting layer.

7. The electronic device according to claim 6, wherein the first layer is n-type organic semiconductor.

8. The electronic device according to claim 6, wherein the second layer is p-type organic semiconductor.

9. The electronic device according to claim 6, wherein the fist layer comprises a material selected from the group consisting of F₁₆—

CuPc, 3,4,9,10-perylene tetracarboxylic acid derivatives, PV, Me-PTC, PTCDA, naphthalenecarboxylic anhydrides, naphthalenecarboxylic diimide, TCNQ, TCE, benzoquinone, 2,6-naphthoquinone, DDQ, p-fluoranil, tetrachlorodiphenoquinone, nickelbisdiphenylglyoxime, BCP, and PBD.

10. The electronic device according to claim 6, wherein the second layer comprises a material selected from the group consisting of CuPc, phthalocyanine bound to a metal, phthalocyanine bound to no metals, TTF, TTT, methylphenothiazine, N-isopropylcarbazole, TPD, and CBP.

11. The electronic device according to claim 6, wherein the acceptor comprises a material selected from the group consisting of AlCl₃, AlBr₃, AsF₆, and halogen.

12. The electronic device according to claim 6, wherein the donor comprises a material selected from the group consisting of K, Ca, Cs, and an alkali earth metal.

13. An electronic device comprising:

a cathode;

an anode;

a structure comprising a first through an n-th functional thin film layers (where n is an integer equal to or greater than

     2) between the cathode and the anode,

a conductive thin film layer between a k-th functional thin film layer (where k is an integer of 1≦

k≦

(n−

1)) and a (k+1)th functional thin film layer,

wherein the conductive thin film layer comprises a first layer in contact with the k-th functional thin film layer and a second layer in contact with the (k+1) th functional thin film layer,

wherein each of the functional thin film layers comprises a light emitting layer,

wherein the first layer and the k-th functional thin film layer comprise at least one of a n-type organic semiconductor and an electron transporting material, and

wherein the second layer and the (k+1)th functional thin film layer comprise at least one of a p-type organic semiconductor and a hole transporting material.

14. The electronic device according to claim 13, wherein the fist layer comprises a material selected from the group consisting of F₁₆—

CuPc, 3,4,9,10-perylene tetracarboxylic acid derivatives, PV, Me-PTC, PTCDA, naphthalenecarboxylic anhydrides, naphthalenecarboxylic diimide, TCNQ, TCE, benzoquinone, 2,6-naphthoquinone, DDQ, p-fluoranil, tetrachlorodiphenoquinone, nickelbisdiphenylglyoxime, BCP, and PBD.

15. The electronic device according to claim 13, wherein the second layer comprises a material selected from the group consisting of CuPc, phthalocyanine bound to a metal, phthalocyanine bound to no metals, TTF, TTT, methylphenothiazine, N-isopropylcarbazole, TPD, and CBP.

16. An electronic device comprising:

a cathode;

an anode;

a structure comprising a first through an n-th functional thin film layers (where n is an integer equal to or greater than

     2) between the cathode and the anode,

a conductive thin film layer between a k-th functional thin film layer (where k is an integer of 1≦

k≦

(n−

1)) and a (k+1)th functional thin film layer,

wherein the conductive thin film layer comprises a first layer including a donor in contact with the k-th functional thin film layer and a second layer including an acceptor in contact with the (k+1) th functional thin film layer,

wherein each of the functional thin film layers comprises a light emitting layer,

wherein the first layer and the k-th functional thin film layer comprise at least one of a n-type organic semiconductor and an electron transporting material,

wherein the first layer is disposed closer to the anode than the second layer, and

wherein the second layer and the (k+1)th functional thin film layer comprise at least one of a p-type organic semiconductor and a hole transporting material.

17. The electronic device according to claim 16, wherein the fist layer comprises a material selected from the group consisting of F₁₆—

CuPc, 3,4,9,10-perylene tetracarboxylic acid derivatives, PV, Me-PTC, PTCDA, naphthalenecarboxylic anhydrides, naphthalenecarboxylic diimide, TCNQ, TCE, benzoquinone, 2,6-naphthoquinone, DDQ, p-fluoranil, tetrachlorodiphenoquinone, nickelbisdiphenylglyoxime, BCP, and PBD.

18. The electronic device according to claim 16, wherein the second layer comprises a material selected from the group consisting of CuPc, phthalocyanine bound to a metal, phthalocyanine bound to no metals, TTF, TTT, methylphenothiazine, N-isopropylcarbazole, TPD, and CBP.

19. The electronic device according to claim 16, wherein the acceptor comprises a material selected from the group consisting of AlCl₃, AlBr₃, AsF₆, and halogen.

20. The electronic device according to claim 16, wherein the donor comprises a material selected from the group consisting of K, Ca, Cs, and an alkali earth metal.

21. An electronic device comprising:

a cathode;

an anode;

a structure comprising a first through an n-th functional thin film layers (where n is an integer equal to or greater than

     2) between the cathode and the anode,

a conductive thin film layer between a k-th functional thin film layer (where k is an integer of 1≦

k≦

(n−

1)) and a (k+1)th functional thin film layer,

wherein the conductive thin film layer contacts with the k-th functional thin film layer and the (k+1)th functional thin film layer,

wherein the conductive thin film layer comprises a first layer including Alq₃ and a second layer including α

-NPD, and

wherein each of the functional thin film layers comprises a light emitting layer.

22. An electronic device comprising:

a cathode;

an anode;

a structure comprising a first through an n-th functional thin film layers (where n is an integer equal to or greater than

     2) between the cathode and the anode,

a conductive thin film layer between a k-th functional thin film layer (where k is an integer of 1≦

k≦

(n−

1)) and a (k+1)th functional thin film layer,

wherein the conductive thin film layer contacts with the k-th functional thin film layer and the (k+1)th functional thin film layer,

wherein the conductive thin film layer comprises a first layer including Li and a second layer including FeCl₃,

wherein the first layer is disposed closer to the anode than the second layer, and

wherein each of the functional thin film layers comprises a light emitting layer.

23. The electronic device according to claim 22, wherein the first layer is n-type organic semiconductor.

24. The electronic device according to claim 22, wherein the second layer is p-type organic semiconductor.

25. The electronic device according to claim 22, wherein the fist layer comprises a material selected from the group consisting of F₁₆—

CuPc, 3,4,9,10-perylene tetracarboxylic acid derivatives, PV, Me-PTC, PTCDA, naphthalenecarboxylic anhydrides, naphthalenecarboxylic diimide, TCNQ, TCE, benzoquinone, 2,6-naphthoquinone, DDQ, p-fluoranil, tetrachlorodiphenoquinone, nickelbisdiphenylglyoxime, BCP, and PBD.

26. The electronic device according to claim 22, wherein the second layer comprises a material selected from the group consisting of CuPc, phthalocyanine bound to a metal, phthalocyanine bound to no metals, TTF, TTT, methylphenothiazine, N-isopropylcarbazole, TPD, and CBP.

27. An electronic device comprising:

a cathode;

an anode;

a structure comprising a first through an n-th functional thin film layers (where n is an integer equal to or greater than

     2) between the cathode and the anode,

a conductive thin film layer between a k-th functional thin film layer (where k is an integer of 1≦

k≦

(n−

1)) and a (k+1)th functional thin film layer,

wherein the conductive thin film layer comprises a first layer in contact with the k-th functional thin film layer and a second layer in contact with the (k+1) th functional thin film layer,

wherein each of the functional thin film layers comprises a light emitting layer,

wherein the first layer and the k-th functional thin film layer comprise Alq₃, and

wherein the second layer and the (k+1)th functional thin film layer comprise α

-NPD.

28. An electronic device comprising:

a cathode;

an anode;

a structure comprising a first through an n-th functional thin film layers (where n is an integer equal to or greater than

     2) between the cathode and the anode,

a conductive thin film layer between a k-th functional thin film layer (where k is an integer of 1≦

k≦

(n−

1)) and a (k+1)th functional thin film layer,

wherein the conductive thin film layer comprises a first layer including Li in contact with the k-th functional thin film layer and a second layer including FeCl₃ in contact with the (k+1) th functional thin film layer,

wherein each of the functional thin film layers comprises a light emitting layer,

wherein the first layer and the k-th functional thin film layer comprise Alq₃,

wherein the first layer is disposed closer to the anode than the second layer, and

wherein the second layer and the (k+1)th functional thin film layer comprise α

-NPD.

29. An electronic device comprising:

a cathode;

an anode;

a first functional thin film layer between the cathode and the anode,

a second functional thin film layer between the cathode and the anode,

a conductive thin film layer between the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer contacts with the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer comprises a first layer and a second layer,

wherein the first layer includes an acceptor, and

wherein each of the first functional thin film layer and the second functional thin film layer comprises a light emitting layer.

30. The electronic device according to claim 29, wherein the first layer is n-type organic semiconductor.

31. The electronic device according to claim 29, wherein the second layer is p-type organic semiconductor.

32. The electronic device according to claim 29, wherein the fist layer comprises a material selected from the group consisting of F₁₆—

CuPc, 3,4,9,10-perylene tetracarboxylic acid derivatives, PV, Me-PTC, PTCDA, naphthalenecarboxylic anhydrides, naphthalenecarboxylic diimide, TCNQ, TCE, benzoquinone, 2,6-naphthoquinone, DDQ, p-fluoranil, tetrachlorodiphenoquinone, nickelbisdiphenylglyoxime, BCP and PBD.

33. The electronic device according to claim 29, wherein the second layer comprises a material selected from the group consisting of CuPc, phthalocyanine bound to a metal, phthalocyanine bound to no metals, TTF, TTT, methylphenothiazine, N-isopropylcarbazole, TPD, and CBP.

34. An electronic device comprising:

a cathode;

an anode;

a first functional thin film layer between the cathode and the anode,

a second functional thin film layer between the cathode and the anode,

a conductive thin film layer between the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer contacts with the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer comprises a first layer including a donor and a second layer including an acceptor,

wherein the first layer is disposed closer to the anode than the second layer, and

wherein each of the first functional thin film layer and the second functional thin film layer comprises a light emitting layer.

35. The electronic device according to claim 34, wherein the first layer is n-type organic semiconductor.

36. The electronic device according to claim 34, wherein the second layer is p-type organic semiconductor.

37. The electronic device according to claim 34, wherein the fist layer comprises a material selected from the group consisting of F₁₆—

CuPc, 3,4,9,10-perylene tetracarboxylic acid derivatives, PV, Me-PTC, PTCDA, naphthalenecarboxylic anhydrides, naphthalenecarboxylic diimide, TCNQ, TCE, benzoquinone, 2,6-naphthoquinone, DDQ, p-fluoranil, tetrachlorodiphenoquinone, nickelbisdiphenylglyoxime, BCP, and PBD.

38. The electronic device according to claim 34, wherein the second layer comprises a material selected from the group consisting of CuPc, phthalocyanine bound to a metal, phthalocyanine bound to no metals, TTF, TTT, methylphenothiazine, N-isopropylcarbazole, TPD, and CBP.

39. The electronic device according to claim 34, wherein the acceptor comprises a material selected from the group consisting of AlCl₃, AlBr₃, AsF₆, and halogen.

40. The electronic device according to claim 34, wherein the donor comprises a material selected from the group consisting of K, Cs, and an alkali earth metal.

41. An electronic device comprising:

a cathode;

an anode;

a first functional thin film layer between the cathode and the anode,

a second functional thin film layer between the cathode and the anode,

a conductive thin film layer between the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer contacts with the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer comprises a first layer and a second layer,

wherein each of the first functional thin film layer and the second functional thin film layer comprises a light emitting layer,

wherein the first layer and the first functional thin film layer comprise at least one of a n-type organic semiconductor and an electron transporting material, and

wherein the second layer and the second functional thin film layer comprise at least one of a p-type organic semiconductor and a hole transporting material.

42. The electronic device according to claim 41, wherein the fist layer comprises a material selected from the group consisting of F₁₆—

CuPc, 3,4,9,10-perylene tetracarboxylic acid derivatives, PV, Me-PTC, PTCDA, naphthalenecarboxylic anhydrides, naphthalenecarboxylic diimide, TCNQ, TCE, benzoquinone, 2,6-naphthoquinone, DDQ, p-fluoranil, tetrachlorodiphenoquinone, nickelbisdiphenylglyoxime, BCP, and PBD.

43. The electronic device according to claim 41, wherein the second layer comprises a material selected from the group consisting of CuPc, phthalocyanine bound to a metal, phthalocyanine bound to no metals, TTF, TTT, methylphenothiazine, N-isopropylcarbazole, TPD, and CBP.

44. An electronic device comprising:

a cathode;

an anode;

a first functional thin film layer between the cathode and the anode,

a second functional thin film layer between the cathode and the anode,

a conductive thin film layer between the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer contacts with the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer comprises a first layer and a second layer,

wherein each of the first functional thin film layer and the second functional thin film layer comprises a light emitting layer,

wherein the first layer and the first functional thin film layer comprise at least one of a n-type organic semiconductor and an electron transporting material,

wherein the first layer is disposed closer to the anode than the second layer, and

wherein the second layer and the second functional thin film layer comprise at least one of a p-type organic semiconductor and a hole transporting material.

45. The electronic device according to claim 44, wherein the fist layer comprises a material selected from the group consisting of F₁₆-CuPc, 3,4,9,10-perylene tetracarboxylic acid derivatives, PV, Me-PTC, PTCDA, naphthalenecarboxylic anhydrides, naphthalenecarboxylic diimide, TCNQ, TCE, benzoquinone, 2,6-naphthoquinone, DDQ, p-fluoranil, tetrachlorodiphenoquinone, nickelbisdiphenylglyoxime, BCP, and PBD.

46. The electronic device according to claim 44, wherein the second layer comprises a material selected from the group consisting of CuPc, phthalocyanine bound to a metal, phthalocyanine bound to no metals, TTF, TTT, methylphenothiazine, N-isopropylcarbazole, TPD, and CBP.

47. The electronic device according to claim 44, wherein the acceptor comprises a material selected from the group consisting of AlCl₃, AlBr₃, AsF₆, and halogen.

48. The electronic device according to claim 44, wherein the donor comprises a material selected from the group consisting of K, Cs, and an alkali earth metal.

49. An electronic device comprising:

a cathode;

an anode;

a first functional thin film layer between the cathode and the anode,

a second functional thin film layer between the cathode and the anode,

a conductive thin film layer between the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer contacts with the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer comprises a first layer including Alq₃ and a second layer including α

-NPD, and

wherein each of the first functional thin film layer and the second functional thin film layer comprises a light emitting layer.

50. An electronic device comprising:

a cathode;

an anode;

a first functional thin film layer between the cathode and the anode,

a second functional thin film layer between the cathode and the anode,

a conductive thin film layer between the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer contacts with the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer comprises a first layer including Li and a second layer including FeCl₃,

wherein the first layer is disposed closer to the anode than the second layer, and

wherein each of the first functional thin film layer and the second functional thin film layer comprises a light emitting layer.

51. The electronic device according to claim 50, wherein the first layer is n-type organic semiconductor.

52. The electronic device according to claim 50, wherein the second layer is p-type organic semiconductor.

53. The electronic device according to claim 50, wherein the fist layer comprises a material selected from the group consisting of F₁₆—

CuPc, 3,4,9,10-perylene tetracarboxylic acid derivatives, PV, Me-PTC, PTCDA, naphthalenecarboxylic anhydrides, naphthalenecarboxylic diimide, TCNQ, TCE, benzoquinone, 2,6-naphthoquinone, DDQ, p-fluoranil, tetrachlorodiphenoquinone, nickelbisdiphenylglyoxime, BCP, and PBD.

54. The electronic device according to claim 50, wherein the second layer comprises a material selected from the group consisting of CuPc, phthalocyanine bound to a metal, phthalocyanine bound to no metals, TTF, TTT, methylphenothiazine, N-isopropylcarbazole, TPD, and CBP.

55. An electronic device comprising:

a cathode;

an anode;

a first functional thin film layer between the cathode and the anode,

a second functional thin film layer between the cathode and the anode,

a conductive thin film layer between the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer contacts with the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer comprises a first layer and a second layer,

wherein each of the first functional thin film layer and the second functional thin film layer comprises a light emitting layer,

wherein the first layer and the first functional thin film layer comprise Alq₃, and

wherein the second layer and the second functional thin film layer comprise α

-NPD.

56. An electronic device comprising:

a cathode;

an anode;

a first functional thin film layer between the cathode and the anode,

a second functional thin film layer between the cathode and the anode,

a conductive thin film layer between the first functional thin film layer and the second functional thin film layer,

wherein the conductive thin film layer comprises a first layer including Li in contact with the first functional thin film layer and a second layer including FeCl₃ in contact with the second functional thin film layer,

wherein each of the first functional thin film layer and the second functional thin film layer comprises a light emitting layer,

wherein the first layer and the first functional thin film layer comprise Alq₃,

wherein the first layer is disposed closer to the anode than the second layer, and

wherein the second layer and the second functional thin film layers comprise α

-NPD.