IP Library › Granted Patent US 10,128,456

Granted Patent B2

US 10,128,456 · App. 14/353,774 · Granted Nov 13, 2018

Organic electroluminescence element, and material for organic electroluminescence element

Inventors: Kazuki Nishimura (Sodegaura, JP); Toshinari Ogiwara (Sodegaura, JP); Kumiko Hibino (Sodegaura, JP); Tetsuya Inoue (Sodegaura, JP); Mitsunori Ito (Sodegaura, JP)

Assignee: IDEMITSU KOSAN CO., LTD.

H01L51/5028 C07D401/10 C07D401/14 C07D403/10 C07D403/14 C07D405/14 C07D409/14 C07D471/04 C07D487/04 C07D491/048 C07F7/0812 C09K11/06 H01L51/0052 H01L51/0054 H01L51/0067 H01L51/0072 H01L51/0073 H01L51/0074 H05B33/10 C09K2211/1007 C09K2211/1011 C09K2211/1029 C09K2211/1044 C09K2211/1088 C09K2211/1092 H01L51/5016 H01L51/5044 H01L2251/5384

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 10,128,456
App. No.: 14/353,774
Granted: Nov 13, 2018
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

The organic electroluminescence device includes an anode, a cathode, and at least an emitting layer between the anode and the cathode. The emitting layer includes a first host material, a second host material, and a phosphorescent dopant material. The first host material is a compound represented by a formula (1) below and the second host material is a compound represented by a formula (2) below.

Claims (247)

1. An organic electroluminescence device, comprising:

an anode;

a cathode; and

at least an emitting layer between the anode and the cathode, the emitting layer comprising:

a first host material;

a second host material; and

a phosphorescent dopant material,

wherein:

the first host material is a compound represented by formula (3):

the second host material is a compound represented by formula (2):

Z 1 represents a cyclic structure fused at a of the formula (3) and is represented by formula (1-1) or (1-2):

Z 2 represents a cyclic structure fused at b of the formula (3) and is represented by the formula (1-1) or (1-2);

at least one of Z 1 and Z 2 is represented by the formula (1-1);

L 1 represents a single bond or a linking group, the linking group being one or a combination of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and a cycloalkyl group having 5 to 30 ring carbon atoms;

m is 1 or 2;

n is 2;

c, d, e, f are fused at a or b in the formula (3);

R 11 and R 31 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

a plurality of R 11 are mutually the same or different;

a plurality of R 31 are mutually the same or different;

adjacent groups of R 11 are optionally bonded with each other to form a ring;

X 1 is a nitrogen atom or C—R 10 and at least one of a plurality of X 1 is a nitrogen atom:

R 1 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

a plurality of R 1 are mutually the same or different;

adjacent groups of R 1 are optionally bonded with each other to form a ring;

R 10 represent the same as R 11 of the formula (1-1);

X 3 is a sulfur atom, an oxygen atom, N—R 32 or C(R 32 ) 2 ;

R 32 represents the same as R 11 and R 31 ; R 2 independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

at least one of R 2 at 2-position, 3-position, 4-position, 5-position, 6-position, and 7-position represents a substituted or unsubstituted 1-carbazolyl group, a substituted or unsubstituted 2-carbazolyl group, a substituted or unsubstituted 3-carbazolyl group, or a substituted or unsubstituted 4-carbazolyl group; R 2 at 1-position and 8-position do not represent a substituted or unsubstituted carbazolyl group;

p and q are 4;

a plurality of R 2 are mutually the same or different;

adjacent groups of R 2 are optionally bonded with each other to form a ring;

L 2 represents a single bond or a linking group, the linking group being one or a combination of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and a cycloalkyl group having 5 to 30 ring carbon atoms; and

FA represents a substituted or unsubstituted fused aromatic cyclic group having 14 to 30 ring carbon atoms, or a substituted or unsubstituted fused aromatic heterocyclic group having 9 to 30 ring atoms except for a substituted or unsubstituted carbazolyl group.

2. The organic electroluminescence device according to claim 1 , wherein the first host material is represented by formula (4):

wherein:

L 1 represents the same as L 1 of the formula (3);

X 1 is a nitrogen atom or C—R 10 and at least one of a plurality of X 1 is a nitrogen atom;

R 1 represents the same as R 1 of the formula (3);

R 10 and R 11 represent the same as R 11 of the formula (1-1);

m is 1 or 2; and

n is 2.

3. The organic electroluminescence device according to claim 1 , wherein:

the first host material is represented by formula (5):

wherein:

L 1 and R 1 respectively represent the same as L 1 and R 1 of the formula (3);

R 11 represents the same as R 11 of the formula (1-1);

L 3 and L 4 represent the same as L 1 of the formula (3);

X 1 is a nitrogen atom or C—R 10 and at least one of a plurality of X 1 is a nitrogen atom:

R 10 represents the same as R 11 of the formula (1-1);

n is 2;

M 3 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

h and k are 4; and

i and j are 3.

4. The organic electroluminescence device according to claim 1 , wherein the second host material is represented by the formula (2) in which FA is a substituted or unsubstituted fused aromatic cyclic group having 2 to 5 fused rings, or a substituted or unsubstituted fused aromatic heterocyclic group having 2 to 5 fused rings.

5. The organic electroluminescence device according to claim 1 wherein:

the second host material is represented by the formula (2) which FA is represented by formula (2-A):

Y represents O, S, or C(R 21 ) 2 ;

R 2 and R 21 represent the same as R 2 of the formula (2);

one of R 2 is a single bond to be bonded with L 2 in the formula (2);

when Y is C(R 21 ) 2 , a plurality of R 21 are mutually the same or different; and

r and s are 4.

6. The organic electroluminescence device according to claim 1 , wherein:

the second host material is represented by the formula (2) in which FA is represented by any one of formulae (2-1), (2-2) and (2-4):

R 2 and R 21 represent the same as R 2 of the formula (2);

one of R 2 is a single bond to be bonded with L 2 in the formula (2); and

r and s are 4.

7. The organic electroluminescence device according to claim 6 , wherein the second host material is represented by the formula (2) in which FA is represented by the formula (2-1) or the formula (2-2).

8. The organic electroluminescence device according to claim 1 , wherein an emission peak wavelength of the phosphorescent dopant material is in a range of 490 nm to 700 nm.

9. A material for an organic electroluminescence device, comprising a compound represented by formula (3) and a compound represented by formula (2):

wherein:

Z 1 represents a cyclic structure fused at a of the formula (3) and represented by formula (1-1) or formula (1-2):

Z 2 represents a cyclic structure fused at b of the formula (3) and represented by the formula (1-1) or the formula (1-2);

at least one of Z 1 and Z 2 is represented by the formula (1-1);

m is 1 or 2;

n is 2; c, d, e, f are fused at a or b in the formula (3);

R 11 and R 31 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group haying 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group haying 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

a plurality of R 11 are mutually the same or different;

a plurality of R 31 are mutually the same or different;

adjacent groups of R 11 are optionally bonded with each other to form a ring;

X 1 is a nitrogen atom or C—R 10 and at least one of a plurality of X 1 is a nitrogen atom;

R 1 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group haying 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

a plurality of R 1 are mutually the same or different;

adjacent groups of R 1 are optionally bonded with each other to form a ring;

R 10 represent the same as R 11 of the formula (1-1);

X 3 is a sulfur atom, an oxygen atom, N—R 32 or C(R 32 ) 2 ;

R 32 represents the same as R 11 and R 31 ,

R 2 independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

at least one of R 2 at 2-position, 3-position, 4-position, 6-position, and 7-position represents a substituted or unsubstituted 1-carbazolyl, a substituted or unsubstituted 2-carbazolyl group, a substituted or unsubstituted 3-carbazolyl group, or a substituted or unsubstituted 4-carbazolyl group;

R 2 at 1-position and 8-position do not represent a substituted or unsubstituted carbazolyl group;

p and q are 4;

a plurality of R 2 are mutually the same or different;

adjacent groups of R 2 are optionally bonded with each other to form a ring;

FA represents a substituted or unsubstituted fused aromatic cyclic group having 14 to 30 ring carbon atoms, and a substituted or unsubstituted fused aromatic heterocyclic group having 9 to 30 ring atoms except for a substituted or unsubstituted carbazolyl group.

10. The material for the organic electroluminescence device according to claim 9 , wherein:

the compound represented by the formula (3) is represented by formula (4):

L 1 represents the same as L 1 of the formula (3);

X 1 is a nitrogen atom or C—R 10 and at least one of a plurality of X 1 is a nitrogen atom;

R 1 represents the same as R 1 of the formula (3);

R 10 and R 11 represent the same as R 11 of the formula (1-1);

m is 1 or 2; and

n is 2.

11. The material for the organic electroluminescence device according to claim 9 , wherein:

the compound represented by the formula (3) is represented by formula (5):

L 1 and R 1 respectively represent the same as L 1 and R 1 of the formula (3);

R 11 represents the same as R 11 of the formula (1-1);

L 3 and L 4 represent the same as L 1 of the formula (3);

X 1 is a nitrogen atom or C—R 10 and at least one of a plurality of X 1 is a nitrogen atom;

R 10 represents the same as R 11 of the formula (1-1);

n is 2;

M 3 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

h and k are 4; and

i and j are 3.

12. The material for the organic electroluminescence device according to claim 9 , wherein the second host material is represented by the formula (2) in which FA is a substituted or unsubstituted fused aromatic cyclic group having 2 to 5 fused rings, or a substituted or unsubstituted fused aromatic heterocyclic group having 2 to 5 fused rings.

13. The material for the organic electroluminescence device according to claim 9 , wherein:

the second host material is represented by the formula (2) in which FA is represented by formula (2-A):

Y represents O, S or C(R 21 ) 2 ;

R 2 and R 21 represent the same as R 2 of the formula (2);

one of R 2 is a single bond to be bonded with L 2 in the formula (2);

when Y is C(R 21 ) 2 , a plurality of R 21 are mutually the same or different; and

r and s are 4.

14. The material for the organic electroluminescence device according to claim 9 , wherein:

the second host material is represented by the formula (2) in which FA is represented by any one of formulae (2-1), (2-2) and (2-4):

R 2 and R 21 represent the same as R 2 of the formula (2);

one of R 2 is a single bond to be bonded with L 2 in the formula (2); and

r and s are 4.

15. The material for the organic electroluminescence device according to claim 14 , wherein the second host material is represented by the formula (2) in which FA is represented by the formula (2-1) or the formula (2-2).

16. The organic electroluminescence device according to claim 2 , wherein R 10 do not represent a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

17. The organic electroluminescence device according to claim 1 , wherein

Z 1 is represented by formula (1-1);

Z 2 is represented by formula (1-2);

R 11 and R 31 each independently represent a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted alkyl group having 1 to 30 carbon atoms;

R 32 each independently represent an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted alkyl group having 1 to 30 carbon atoms;

at least two of a plurality of X 1 are each a nitrogen atom;

the rest of X 1 is C—R 10 , wherein R 10 is a hydrogen atom;

R 1 each independently represent an unsubstituted aryl group having 6 to 30 ring carbon atoms;

L 1 represents a single bond or an unsubstituted aryl group having 6 to 30 ring carbon atoms;

L 2 represents a single bond or an unsubstituted aryl group having 6 to 30 ring carbon atoms;

one of R 2 at 2-position, 3-position, 4-position, 5-position, 6-position, and 7-position

represents a substituted or unsubstituted 1-carbazolyl group, a substituted or unsubstituted 2-carbazolyl group, a substituted or unsubstituted 3-carbazolyl group, or a substituted or unsubstituted 4-carbazolyl group;

R 2 at 1-position and 8-position represent a hydrogen atom;

the rest of R 2 each independently represent a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted alkyl group having 1 to 30 carbon atoms; and

FA represents an unsubstituted fused aromatic cyclic group having 14 to 30 ring carbon atoms, or an unsubstituted fused aromatic heterocyclic group having 9 to 30 ring atoms.

18. The organic electroluminescence device according to claim 1 , wherein

Z 1 is represented by formula (1-1)

Z 2 is represented by formula (1-2)

R 11 and R 31 represent a hydrogen atom;

R 32 each independently represent an unsubstituted phenyl group or an unsubstituted methyl group;

all of X 1 are nitrogen atoms;

R 1 each independently represent an unsubstituted phenyl group or an unsubstituted biphenyl group;

L 1 represents a single bond or an unsubstituted phenyl group;

m is 1;

L 2 represents a single bond or an unsubstituted phenyl group;

one of R 2 at 2-position, 3-position, 4-position, 5-position, 6-position, and 7-position

represents a 1-carbazolyl group having a substituted or unsubstituted phenyl group, a 2-carbazolyl group having a substituted or unsubstituted phenyl group, a 3-carbazolyl group having a substituted or unsubstituted phenyl group, or a 4-carbazolyl group having a substituted or unsubstituted phenyl group;

the rest of R 2 represent a hydrogen atom; and

FA represents an unsubstituted fused aromatic cyclic group having 14 to 20 ring carbon atoms, or an unsubstituted fused aromatic heterocyclic group having 9 to 14 ring atoms.

19. The organic electroluminescence device according to claim 1 , wherein

Z 1 is represented by formula (1-1);

R 11 each independently represent a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or a carbazolyl group having an unsubstituted phenyl group;

R 31 each independently represent a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted alkyl group having 1 to 30 carbon atoms;

R 32 each independently represent an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted alkyl group having 1 to 30 carbon atoms;

at least two of a plurality of X 1 are each a nitrogen atom;

the rest of X 1 is C—R 10 , wherein R 10 is a hydrogen atom;

R 1 each independently represent an unsubstituted aryl group having 6 to 30 ring carbon atoms;

L 1 represents a single bond or an unsubstituted aryl group having 6 to 30 ring carbon atoms;

L 2 represents a single bond or an unsubstituted aryl group having 6 to 30 ring carbon atoms;

one of R 2 at 2-position, 3-position, 4-position, 5-position, 6-position, and 7-position

represents a substituted or unsubstituted 1-carbazolyl group, a substituted or unsubstituted 2-carbazolyl group, a substituted or unsubstituted 3-carbazolyl group or a substituted or unsubstituted 4-carbazolyl group;

R 2 at 1-position and 8-position represent a hydrogen atom;

the rest of R 2 each independently represent a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted alkyl group having 1 to 30 carbon atoms; and

FA represents an unsubstituted fused aromatic cyclic group having 14 to 30 ring carbon atoms, or an unsubstituted fused aromatic heterocyclic group having 9 to 30 ring atoms.

20. The organic electroluminescence device according to claim 1 , wherein

Z 1 is represented by formula (1-1)

Z 2 is represented by formula (1-2);

R 31 represent a hydrogen atom;

R 32 each independently represent an unsubstituted phenyl group or an unsubstituted methyl group;

at least two of a plurality of X 1 are each a nitrogen atom;

the rest of X 1 is C—R 10 , wherein R 10 is a hydrogen atom;

R 1 each independently represent an unsubstituted phenyl group or an unsubstituted biphenyl group;

L 1 represents a single bond or an unsubstituted phenyl group;

L 2 represents a single bond or an unsubstituted phenyl group;

one of R 2 at 2-position, 3-position, 4-position, 5-position, 6-position, and 7-position

the rest of R 2 represent a hydrogen atom; and

FA represents an unsubstituted fused aromatic cyclic group having 14 to 20 ring carbon atoms, or an unsubstituted fused aromatic heterocyclic group having 9 to 14 ring atoms.

21. The material for the organic electroluminescence device according to claim 9 , wherein

Z 1 is represented by formula (1-1);

Z 2 is represented by formula (1-2);

R 11 and R 31 each independently represent a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted alkyl group having 1 to 30 carbon atoms:

R 32 each independently represent an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted alkyl group having 1 to 30 carbon atoms;

at least two of a plurality of X 1 are each a nitrogen atom;

the rest of X 1 is C—R 10 , wherein R 10 is a hydrogen atom;

R 1 each independently represent an unsubstituted aryl group having 6 to 30 ring carbon atoms;

L 1 represents a single bond or an unsubstituted aryl group having 6 to 30 ring carbon atoms;

L 2 represents a single bond or an unsubstituted aryl group having 6 to 30 ring carbon atoms;

one of R 2 at 2-position, 3-position, 4-position, 5-position, 6-position, and 7-position

R 2 at 1-position and 8-position represent a hydrogen atom;

the rest of R 2 each independently represent a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted alkyl group having 1 to 30 carbon atoms; and

FA represents an unsubstituted fused aromatic cyclic group having 14 to 30 ring carbon atoms, or an unsubstituted fused aromatic heterocyclic group having 9 to 30 ring atoms.

22. The material for the organic electroluminescence device according to claim 9 , wherein

Z 1 is represented by formula (1-1);

Z 2 is represented by formula (1-2);

R 11 and R 31 represent a hydrogen atom;

R 32 each independently represent an unsubstituted phenyl group or an unsubstituted methyl group;

all of X 1 are nitrogen atoms;

R 1 each independently represent an unsubstituted phenyl group or an unsubstituted biphenyl group;

L 1 represents a single bond or an unsubstituted phenyl group;

m is 1;

L 2 represents a single bond or an unsubstituted phenyl group;

one of R 2 at 2-position, 3-position, 4-position, 5-position, 6-position, and 7-position

represents a 1-carbazolyl group haying a substituted or unsubstituted phenyl group, a 2-carbazolyl group haying a substituted or unsubstituted phenyl group, a 3-carbazolyl group having a substituted or unsubstituted phenyl group, or a 4-carbazolyl group having a substituted or unsubstituted phenyl group;

the rest of R 2 represent a hydrogen atom; and

FA represents an unsubstituted fused aromatic cyclic group having 14 to 20 ring carbon atoms, or an unsubstituted fused aromatic heterocyclic group having 9 to 14 ring atoms.

23. The material for the organic electroluminescence device according to claim 9 , wherein