IP Library Granted Patent US 7,615,289
Granted Patent B2
US 7,615,289 · App. 10/596,842 · Granted Nov 10, 2009

Organic electroluminescent polymer having 9,9-di(fluorenyl)-2,7-fluorenyl unit and organic electroluminescent device manufactured using the same

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Quick Facts
Patent No.
US 7,615,289
App. No.
10/596,842
Granted
Nov 10, 2009
Kind
B2
Abstract

Disclosed herein is an organic electroluminescent polymer having 9,9-di(fluorenyl)-2,7-fluorenyl unit and an electroluminescent device using the same. Specifically, the current invention provides an organic electroluminescent polymer having 9,9-di(fluorenyl)-2,7-fluorenyl unit, which can be used as a blue electroluminescent polymer and host material by introducing the substituted fluorenyl group at the 9-position of fluorene, and an electroluminescent device using the electroluminescent polymer. The electroluminescent polymer is applicable as a host material for highly pure blue, green and red, having high solubility, high heat stability and high quantum efficiency.

Claims (34)

1. An organic electroluminescent polymer having 9,9-di(fluorenyl)-2,7-fluorenyl unit represented by the following Formula 1:

wherein, R 1 , R 2 , R 3 and R 4 are the same or different, each being a linear or branched alkyl group of 1-20 carbons; an aryl group which is unsubstituted or substituted with at least one substituent group selected from the group consisting of linear or branched alkyl and alkoxy groups of 1-20 carbons; a linear or branched alkyl group of 1-20 carbons having at least one hetero-atom selected from the group consisting of F, S, N, O, P and Si; an aryl group which is substituted with at least one substituent group selected from the group consisting of linear or branched alkyl and alkoxy groups of 1-20 carbons containing at least one hetero-atom selected from the group consisting of F, S, N, O, P and Si; an aryl group having a heterocyclic moiety of 2-24 carbons which is unsubstituted or substituted with at least one substituent group selected from the group consisting of linear or branched alkyl and alkoxy groups of 1-20 carbons; an aryl group having a heterocyclic moiety of 2-24 carbons which is substituted with at least one substituent group selected from the group consisting of linear or branched alkyl and alkoxy groups of 1-20 carbons containing at least one hetero-atom selected from the group consisting of F, S, N, O, P and Si; a substituted or unsubstituted trialkylsilyl group of 3-40 carbons; a substituted or unsubstituted arylsilyl group of 3-40 carbons; a substituted or unsubstituted carbazole group of 12-60 carbons; a substituted or unsubstituted phenothiazine group of 6-60 carbons; or a substituted or unsubstituted arylamine group of 6-60 carbons; R 5 , R 6 , R 7 and R 8 are the same or different, each being hydrogen; a linear or branched alkyl or alkoxy group of 1-20 carbons; an aryl group which is unsubstituted or substituted with at least one substituent group selected from the group consisting of linear or branched alkyl and alkoxy groups of 1-20 carbons; a linear or branched alkyl or alkoxy group of 1-20 carbons having at least one hetero-atom selected from the group consisting of F, S, N, O, P and Si; an aryl group which is substituted with at least one substituent group selected from the group consisting of linear or branched alkyl and alkoxy groups of 1-20 carbons containing at least one hetero-atom selected from the group consisting of F, S, N, O, P and Si; an aryl group having a heterocyclic moiety of 2-24 carbons which is unsubstituted or substituted with at least one substituent group selected from the group consisting of linear or branched alkyl and alkoxy groups of 1-20 carbons; an aryl group having a heterocyclic moiety of 2-24 carbons which is substituted with at least one substituent group selected from the group consisting of linear or branched alkyl and alkoxy groups of 1-20 carbons containing at least one hetero-atom selected from the group consisting of F, S, N, O, P and Si; a substituted or unsubstituted trialkylsilyl group of 3-40 carbons; a substituted or unsubstituted arylsilyl group of 3-40 carbons; a substituted or unsubstituted carbazole group of 12-60 carbons; a substituted or unsubstituted phenothiazine group of 6-60 carbons; or a substituted or unsubstituted arylamine group of 6-60 carbons; a, b, c and d are the same or different, each being an integer of 1-3; Ar is selected from the group consisting of a substituted or unsubstituted aromatic moiety of 6-60 carbons, a substituted or unsubstituted heteroaromatic moiety of 2-60 carbons, and combinations thereof; and

l is an integer of 1-100,000, m is an integer of 0-100,000, and n is an integer of 1-100,000.

2. The organic electroluminescent polymer as set forth in claim 1 , wherein said R 1 , R 2 , R 3 and R 4 , respectively are selected from the following group:

3. The organic electroluminescent polymer as set forth in claim 1 , wherein said R 5 and R 6 , respectively are selected from the following group:

H,

wherein, R 9 and R 10 are the same or different, and respectively are a linear or branched alkyl group of 1-20 carbons;

R 11 is hydrogen or a linear or branched alkyl, alkoxy or trialkylsilyl group of 1-20 carbons;

R 12 and R 13 are the same or different, and respectively are a linear or branched alkyl group of 1-20 carbons;

R 14 , R 15 and R 16 are the same or different, and respectively are a linear or branched alkyl or alkoxy group of 1-20 carbons; or an aryl group which is unsubstituted or substituted with at least one substituent group selected from the group consisting of linear or branched alkyl and alkoxy groups of 1-20 carbons;

R 17 , R 18 , R 19 , R 20 , R 21 and R 22 are the same or different, and respectively are hydrogen; a linear or branched alkyl or alkoxy group of 1-20 carbons; or an aryl group which is unsubstituted or substituted with at least one substituent group selected from the group consisting of linear or branched alkyl and alkoxy groups of 1-20 carbons;

X is O or S;

Y and Z are N; and

a is an integer of 1-3.

4. The organic electroluminescent polymer as set forth in claim 1 , wherein said R 7 and R 8 , respectively are selected from the following group:

H,

5. The organic electroluminescent polymer as set forth in claim 1 , wherein said Ar is selected from the following group:

(i) a substituted or unsubstituted arylene group of 6-60 carbons;

(ii) a substituted or unsubstituted heterocyclic arylene group of 2-60 carbons in which at least one hetero-atom selected from the group consisting of N, S, O, P and Si is incorporated in an aromatic ring;

(iii) a substituted or unsubstituted arylenevinylene group of 6-60 carbons;

(iv) a substituted or unsubstituted arylamine group of 6-60 carbons;

(v) a substituted or unsubstituted carbazole group of 12-60 carbons; and

(vi) combinations thereof,

in which Ar may include a substituent selected from the group consisting of a linear or branched alkyl or alkoxy group of 1-20 carbons; an aryl group which is unsubstituted or substituted with at least one substituent group selected from the group consisting of linear or branched alkyl and alkoxy groups of 1-20 carbons; a cyano group (—CN); and a silyl group.

6. The organic electroluminescent polymer as set forth in claim 5 , wherein said Ar is present in an amount of 5-15 mol % in the electroluminescent polymer, with proviso of being a substituted or unsubstituted arylamine group of 6-60 carbons.

7. The organic electroluminescent polymer as set forth in claim 1 , wherein a ratio of 1:m ranges from 5:95 to 95:5.

8. The organic electroluminescent polymer as set forth in claim 1 , wherein the organic electroluminescent polymer has the following Formula 2:

wherein, n 1 is an integer from 1 to 100,000.

9. The organic electroluminescent polymer as set forth in claim 1 , wherein the organic electroluminescent polymer has the following Formula 3:

wherein, l 1 is an integer from 1 to 100,000, and m 1 is an integer from 1 to 100,000.

10. The organic electroluminescent polymer as set forth in claim 1 , wherein the organic electroluminescent polymer has the following Formula 4:

wherein, l 2 is an integer from 1 to 100,000, and m 2 is an integer from 1 to 100,000.

11. An organic electroluminescent device having at least one layer comprising the polymer according to claim 1 between an anode and a cathode, wherein, the layer is a hole-transport layer, a light emitting layer, an electron-transport layer or a hole blocking layer.

12. The organic electroluminescent device as set forth in claim 11 , wherein the electroluminescent device comprises a structure of anode/light emitting layer/cathode, anode/hole transport layer/light emitting layer/cathode, or anode/hole transport layer/light emitting layer/electron transport layer/cathode.

Assignments (6)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED ON REEL 026576 FRAME 0776. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded May 24, 2017
From: SK ENERGY CO., LTD.
To: SK INNOVATION CO., LTD.
Reel/Frame 042553/0926 →
CHANGE OF NAME Recorded Jul 12, 2011
From: SK ENERGY CO., LTD
To: SK INNOVATION CO., LTD.
Reel/Frame 026576/0776 →
CORRECTIVE ASSIGNMENT TO CORRECT SERIAL NUMBER 10/596,842, PREVIOUSLY RECORDED AT REEL 019558 FRAME 0665. Recorded Apr 22, 2008
From: NIIYAMA, EISUKE
To: KIKUCHI, AYAKO; ANZAI, KOUICHI; ITAMURA, MASAYUKI; KIKUCHI, MASAO
Reel/Frame 020903/0652 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2007
From: SK CORPORATION
To: SK ENERGY CO., LTD
Reel/Frame 020249/0017 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2007
From: NIIYAMA, EISUKE
To: KIKUCHI, AYAKO; ANZAI, KOUICHI; ITAMURA, MASAYUKI; KIKUCHI, MASAO
Reel/Frame 019558/0665 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2006
From: YOU, HONG; CHOI, WEON JUNG; SHIN, DONG CHEOL; LEE, SANG SOO; JIN, JAE KYU; KIM, JONG WOOK; KWON, SOON KI; KIM, YUN HI
To: SK CORPORATION
Reel/Frame 017888/0318 →