Polymer Compound and Polymer Light Emitting Device Using the Same

• US 20080088228A1
• Filed: 12/26/2005
• Published: 04/17/2008
• Est. Priority Date: 12/27/2004
• Status: Active Grant

• Current Assignee: Sumitomo Chemical Company Limited
• Original Assignee: Dsumitomo Chemical Company Limited
• Inventors: Suzuki, Tomoyuki, Noguchi, Takanobu, Kakimoto, Hidenobu
• Granted Patent: US 8,293,380 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C08G 61/122 derived from five- or six-membered heterocyclic compounds, other than imides
• CPC Class Codes: C08G 73/0688 with only one nitrogen atom in the ring, e.g. polyquinolines
• CPC Class Codes: C09D 11/102 containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: G02F 1/133603 with LEDs
• CPC Class Codes: G02F 2202/022 polymeric
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/115 Polyfluorene; Derivatives thereof
• CPC Class Codes: H10K 85/151 Copolymers
• CPC Class Codes: H10K 85/342 comprising iridium

Abstract

A polymer compound containing a structure of the following formula (B):
—Ar—  (A)
(wherein, Ar represents an arylene group, divalent heterocyclic group, divalent aromatic amine group or divalent group having a metal complex structure.)
(wherein, A ring and B ring represent each independently an aromatic ring optionally having a substituent. X₁ represents —C(═O)—, —S(═O)—, —S(═O)₂—, —P(═O)(R₁)—, —C(R₁)(R₂)—, —C(R₂)(R₂)—, —B(R₁)—, —N(R₁)— or —Si(R₁)(R₁)—. R* represents a hydrogen atom or monovalent or divalent group, R₁ represents a hydrogen atom or monovalent group, and R₂ represents a monovalent group having a hetero atom. When R₁ and R₂ are present each in plural number, they may be the same or different.).

Claims

1. A polymer compound having one or more repeating units of the following formula (A) and containing further a structure of the following formula (B):

—

Ar—

 

 

(A)

wherein, Ar represents an arylene group, divalent heterocyclic group, divalent aromatic amine group or divalent group having a metal complex structure

wherein, A ring and B ring represent each independently an aromatic ring optionally having a substituent, X represents —

C(═

O)—

, —

S(═

O)—

, —

S(═

O)₂—

, —

P(═

O)(R₁)—

, —

C(R₁)(R₂)—

, —

C(R₂)(R₂)—

, —

B(R₁)—

, —

N(R₁)—

or —

Si(R₁)(R₁)—

, R* represents a hydrogen atom or monovalent or divalent group, R₁ represents a hydrogen atom or monovalent group, and R₂ represents a monovalent group having a hetero atom, and when R₁ and R₂ are present each in plural number, they may be the same or different.

2. The polymer compound according to claim 1 wherein the light emitting wavelength of a polymer compound composed of a structure of said formula (B) is longer by 30 nm or more than the light emitting wavelength of a polymer compound composed of a structure of said formula (A).

3. The polymer compound according to claim 1, having a structure of the following formula (1):

wherein, A₁ represents a hydrogen atom, alkyl group, aryl group, arylalkyl group, aryloxyalkyl group, monovalent heterocyclic group or divalent group, R represents a hydrogen atom, alkyl group, alkoxy group, alkylthio group, alkylsilyl group, alkylamino group, aryl group, aryloxy group, arylalkyl group, arylalkoxy group, arylalkenyl group, arylalkynyl group, arylamino group, monovalent heterocyclic group or cyano group, Z*s represent each independently a direct bond or R, J and K represent each independently an integer from 0 to 3, J1 and K1 represent each independently 0 or 1, and when a plurality of Rs are present, they may be the same or different.

4. The polymer compound according to claim 3, containing a repeating unit of the following formula (2):

wherein, Z represents —

CR₃═

CR₄—

or —

C≡

C, R₃ and R₄ represent each independently a hydrogen atom, alkyl group, aryl group, monovalent heterocyclic group or cyano group, j and k represent each independently an integer of 0 to 3, m represents 0 or 1, and A1 and R are as described above.

5. The polymer compound according to claim 4, further containing a repeating unit of the following formula (30):

—

Ar₁-(Z′

)_p- 

 

(30)

wherein, Ar₁ represents an arylene group, divalent heterocyclic group or divalent aromatic amine group, Z′

represents —

CR₅═

CR₆—

or —

C≡

C, R₅ and R₆ represent each independently a hydrogen atom, alkyl group, aryl group, monovalent heterocyclic group or cyano group, and p represents 0 or 1.

7. The polymer compound according to claim 3, containing a repeating unit of the following formula (3):

wherein A₂s represent each independently a group of the following formula (4);

*—

(Ar₁)j₁-(X)k₁-(Ar₂)p₁-(Y)q₁- 

 

(4)

wherein, Ar₁ and Ar₂ represent each independently an arylene group, divalent heterocyclic group or divalent aromatic amine group, X represents —

R₇—

, —

O—

R₇—

, —

R₇—

O—

, —

R₇—

C(O)O—

, —

R₇—

OC(O)—

, —

R₇—

N(R₂₀)—

, —

O—

, —

S—

, —

C(O)O—

or —

C(O)—

, Y represents —

C(R₂₀)═

C(R₂₀)—

or —

C≡

C—

, j₁, k₁, p₁ and q₁ are each independently 0 or 1, R₇ represents an alkylene group, R₂₀ represents a hydrogen atom, alkyl group, aryl group, monovalent heterocyclic group or cyano group, and * represents a site to be connected to N, n₁ and n₂ represent each independently 0 or 1, and R is as described above, and a plurality of Rs may be the same or different.

8. The polymer compound according to claim 7, further containing a repeating unit of the following formula (31):

—

Ar₄-(Z″

)_t- 

 

(31)

wherein, Ar₄ represents an arylene group, divalent heterocyclic group or divalent aromatic amine group, Z″

represents —

CR₈═

CR₉—

or —

C≡

C, R₈ and R₉ represent each independently a hydrogen atom, alkyl group, aryl group, monovalent heterocyclic group or cyano group, and t represents 0 or 1.

10. The polymer compound according to claim 1, wherein the polystyrene reduced number average molecular weight is 10³ to 10⁸.

11. A composition comprising at least one material selected from the group consisting of hole transporting materials, electron transporting materials and light emitting materials and at least one of the polymer compound according to claim 1.

12. An ink composition comprising the polymer compound according to claim 1.

13. A thin film comprising the polymer compound according to claim 1.

14. An electrically conductive thin film comprising the polymer compound according to claim 1.

15. An organic semiconductor thin film comprising the polymer compound according to claim 1.

16. An organic transistor having the organic semiconductor thin film according to claim 15.

17. A polymer light emitting device having an organic layer containing the polymer compound according to claim 1 between electrodes composed of an anode and a cathode.

18. The polymer light emitting device according to claim 17 wherein said organic layer is a light emitting layer.

19. The polymer light emitting device according to claim 18 wherein said light emitting layer contains further a hole transporting material, electron transporting material or light emitting material.

20. The polymer light emitting device according to claim 17 wherein a light emitting layer and a charge transporting layer are present between the electrodes composed of an anode and a cathode and the charge transporting layer contains a polymer compound one or more repeating units of the following formula (A) and containing further a structure of the following formula (B):

—

Ar—

 

 

(A)

wherein, Ar represents an arylene group, divalent heterocyclic group, divalent aromatic amine group or divalent group having a metal complex structure,

wherein, A ring and B ring represent each independently an aromatic ring optionally having a substituent, X represents —

C(═

O)—

, —

S(═

O)—

, —

S(═

O)—

, —

P(═

O)(R₁)—

, —

C(R₁)(R₂)—

, —

C(R₂)(R₂)—

, —

B(R₁)—

, —

N(R₁)—

or —

Si(R₁)(R₁)—

, R* represents a hydrogen atom or monovalent or divalent group, R₁ represents a hydrogen atom or monovalent group, and R₂ represents a monovalent group having a hetero atom, and when R₁, and R₂ are present each in plural number, they may be the same or different.

21. The polymer light emitting device according to claim 17 wherein a light emitting layer and a charge transporting layer are present between the electrodes composed of an anode and a cathode, a charge injection layer is present between the charge transporting layer and the electrode and the charge injection layer contains a polymer compound one or more repeating units of the following formula (A) and containing further a structure of the following formula (B):

—

Ar—

 

 

(A)

wherein, Ar represents an arylene group, divalent heterocyclic group, divalent aromatic amine group or divalent group having a metal complex structure,

wherein, A ring and B ring represent each independently an aromatic ring optionally having a substituent, X represents —

C(═

O)—

, —

S(═

O)—

, —

S(═

O)₂—

, —

P(═

O)(R₁)—

, —

C(R₁)(R₂)—

, —

C(R₂)(R₂)—

, —

B(R₁)—

, —

N(R₁)—

or —

Si(R₁)(R₁)—

, R* represents a hydrogen atom or monovalent or divalent group, R₁ represents a hydrogen atom or monovalent group, and R₂ represents a monovalent group having a hetero atom, and when R₁ and R₂ are present each in plural number, they may be the same or different.

22. A sheet light source using the polymer light emitting device according to claim 17.

23. A segment display using the polymer light emitting device according to claim 17.

24. A dot matrix display using the polymer light emitting device according to claim 17.

25. A liquid crystal display using as backlight the polymer light emitting device according to claim 17.

6. A polymer compound composed of a repeating unit of said formula (2) wherein m is 0.

9. A polymer compound composed of a repeating unit of said formula (3) wherein n₁ and n₂ are both 0.