IP Library Granted Patent US 9,147,847
Granted Patent B2
US 9,147,847 · App. 14/487,768 · Granted Sep 29, 2015

Anthracene derivative and organic electroluminescent element using the same

Inventors: Masahiro Kawamura (Sodegaura, JP); Chishio Hosokawa (Sodegaura, JP); Masaki Numata (Sodegaura, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
H01L51/0058C07D307/77C07D307/79C07D307/91C07D307/92C07D333/50C07D333/74C07D333/76C07D493/04C07D519/00C09K11/06H01L51/006H01L51/0052H01L51/0073H01L51/0074C09K2211/1011C09K2211/1014H01L51/5012
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Quick Facts
Patent No.
US 9,147,847
App. No.
14/487,768
Granted
Sep 29, 2015
Kind
B2
Abstract

An anthracene derivative represented by the following formula (1): In the formula (1), Z is a structure represented by the following formula (2). In the formula (2), at least one pair of adjacent two substituents of R 11 to R 18 form a ring represented by the following formula (3) or (4):

Claims (27)

1. An organic electroluminescence device which comprises between an anode and a cathode one or more organic thin film layers comprising an emitting layer, wherein the emitting layer comprises an anthracene derivative represented by the following formula (1) as a host material and a fused polycyclic amine derivative represented by the following formula (12) as a dopant material:

wherein in the formula (1), at least one of R 1 to R 10 is used for bonding to L 1 , the one used for bonding to L 1 is a single bond, R 1 to R 10 which are not used for bonding to L 1 are independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;

L 1 is a single bond or a linkage group;

a, b and c are independently an integer of 1 to 4; and

Z is represented by any of the following formulas (8) to (10):

wherein in the formulas (8) to (10), R 201 to R 210 , R 211 to R 220 and R 221 to R 230 are independently a hydrogen atom or a substituent; any one of R 201 to R 210 , anyone of R 211 to R 220 and anyone of R 221 to R 230 are used for bonding to L 1 ; and the ones used for bonding to L 1 are a single bond; and

X 1 is an oxygen atom or a sulfur atom:

wherein in the formula (12), Y is a substituted or unsubstituted fused aryl group having 10 to 50 ring carbon atoms; Ar 101 and Ar 102 are independently an aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and n is an integer of 1 to 4.

2. The organic electroluminescence device according to claim 1 , wherein Z is represented by the formula (9) in the formula (1).

3. The organic electroluminescence device according to claim 2 , wherein b is 1 in the formula (1).

4. The organic electroluminescence device according to claim 2 , wherein a is 1 or 2 in the formula (1).

5. The organic electroluminescence device according to claim 2 , wherein L 1 is bonded to R 5 and/or R 10 in the formula (1).

6. The organic electroluminescence device according to claim 2 , wherein L 1 is bonded to any of R 1 to R 4 in the formula (1).

7. The organic electroluminescence device according to claim 6 , wherein L 1 is bonded to R 2 in the formula (1).

8. The organic electroluminescence device according to claim 6 , wherein R 5 in the formula (1) is a group selected from a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

9. The organic electroluminescence device according to claim 6 , wherein R 5 and/or R 10 in the formula (1) is a group selected from a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

10. The organic electroluminescence device according to claim 8 , wherein R 5 in the formula (1) has a structure represented by the following formula (11):

wherein in the formula (11), Ar 1 is a group selected from a substituted or unsubstituted aryl group having 6 to 80 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 80 ring atoms; Ra is independently a hydrogen atom or a substituent; and d is an integer of 1 to 4.

11. The organic electroluminescence device according to claim 8 , wherein R 5 in the formula (1) is a substituted or unsubstituted fused aromatic ring having 10 to 30 ring carbon atoms.

12. The organic electroluminescence device according to claim 2 , wherein X 1 is oxygen atom in the formula (9).

13. The organic electroluminescence device according to claim 1 , wherein the dopant material is a fused polycyclic amine derivative which is represented by the following formula (13):

wherein in the formula (13), R e is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms or a substituted or unsubstituted arylgermanium group having 6 to 50 ring carbon atoms; t is an integer of 1 to 10; and Ar 201 to Ar 204 are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

14. The organic electroluminescence device according to claim 1 , wherein the dopant material is a fused polycyclic amine derivative which is represented by the following formula (14):

wherein in the formula (14), R f is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms or a substituted or unsubstituted arylgermanium group having 6 to 50 ring carbon atoms; u is an integer of 1 to 8; and Ar 205 to Ar 208 are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

15. The organic electroluminescence device according to claim 14 , wherein Ar 205 to Ar 208 in the formula (14) are independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted dibenzofuranyl group.

16. The organic electroluminescence device according to claim 1 which has a hole-injecting layer between the anode and the emitting layer.

17. The organic electroluminescence device according to claim 1 , wherein Y in the formula (12) is a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group or a substituted or unsubstituted chrysenyl group.

Priority Claims (1)
JP 2009-131200 · May 29, 2009 · national
Continuity (3)
Continuation 14093325 · Nov 29, 2013
Continuation 13375020
Related Publication 20150005512A1 · Jan 1, 2015