IP Library › Granted Patent US 9,923,148
Granted Patent B2
US 9,923,148 · App. 13/654,550 · Granted Mar 20, 2018

Electroluminescent device

Inventors: Thomas Schafer (Basel, CH); Patrice Bujard (Coutrepin, CH); Jonathan Rogers (White Plains, NY); Kristina Bardon (Waldshut, DE)
Assignee: UDC Ireland Limited
H01L51/0067C07D239/26C07D403/10C09K11/06C09K2211/1018
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Quick Facts
Patent No.
US 9,923,148
App. No.
13/654,550
Granted
Mar 20, 2018
Kind
B2
Abstract

Disclosed are electroluminescent devices that comprise organic layers that contain certain organic compounds containing one or more pyrimidine moieties. The organic compounds containing one or more pyrimidine moieties are suitable components of blue-emitting, durable, organo-electroluminescent layers. The electroluminescent devices may be employed for full color display panels in for example mobile phones, televisions and personal computer screens.

Claims (508)

1. A pyrimidine compound of formula (VI) or (VII)

where Ar is a group of formula

W 11 to W 15 , W 21 to W 25 , W 31 to W 35 , W 41 to W 45 , Y 11 to Y 15 , Y 21 to Y 25 , Y 31 to Y 35 and Y 41 to Y 45 are independently of each other H; C 6 -C 24 aryl; C 6 -C 24 aryl which is substituted by G; C 1 -C 18 alkyl; C 1 -C 18 alkyl which is substituted by E and/or interrupted by D; C 7 -C 18 alkylaryl; C 7 -C 18 alkylaryl which is substituted by E and/or interrupted by D; C 2 -C 18 alkenyl; C 2 -C 18 alkenyl which is substituted by E and/or interrupted by D; C 2 -C 18 alkynyl; C 2 -C 18 alkynyl which is substituted by E and/or interrupted by D; C 1 -C 18 alkoxy; C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D; —SR 5 ; —NR 5 R 6 ; C 2 -C 24 heteroaryl; C 2 -C 24 heteroaryl which is substituted by L; —SOR 4 ; —SO 2 R 4 ; —COR 5 ; —COOR 7 ; —CONR 5 R 6 ; C 4 -C 18 cycloalkyl; C 4 -C 18 cycloalkyl which is substituted by E and/or interrupted by D; C 4 -C 18 cycloalkenyl; C 4 -C 18 cycloalkenyl which is substituted by E and/or interrupted by D;

V is H;

A 18 and A 19 are independently of each other H; C 1 -C 18 alkyl; C 1 -C 18 alkyl which is substituted by E and/or interrupted by D; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by E,

B 11 to B 14 and B 21 to B 24 are independently of each other H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by G; C 1 -C 18 alkyl; C 1 -C 18 alkyl which is substituted by E and/or interrupted by D; C 7 -C 18 alkylaryl; C 7 -C 18 alkylaryl which is substituted by E and/or interrupted by D; C 2 -C 18 alkenyl; C 2 -C 18 alkenyl which is substituted by E and/or interrupted by D; C 2 -C 18 alkynyl; C 2 -C 18 alkynyl which is substituted by E and/or interrupted by D; C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D; —SR 5 ; —NR 5 R 6 ; C 2 -C 18 heteroaryl; C 2 -C 18 heteroaryl which is substituted by L; —SOR 4 ; —SO 2 R 4 ; —COR 8 ; —COOR 7 ; —CONR 5 R 6 ; C 4 -C 18 cycloalkyl; C 4 -C 18 cycloalkyl which is substituted by E and/or interrupted by D; C 4 -C 18 cycloalkenyl; C 4 -C 18 cycloalkenyl which is substituted by E and/or interrupted by D;

D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO 2 —; —O—; —NR 5 —; —SiR 5 R 6 —; —POR 5 —; —CR 5 ═CR 6 — or —C≡C—;

E is —OR 5 ; —SR 5 ; —NR 5 R 6 ; —COR 8 ; —COOR 7 ; —CONR 5 R 6 ; —CN; —OCOOR 7 or halogen;

G is E; K; heteroaryl; heteroaryl which is substituted by C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by E or K;

K is C 1 -C 18 alkyl; C 1 -C 18 alkyl which is substituted by E or interrupted by D; C 7 -C 18 alkylaryl which is substituted by E or interrupted by D; C 2 -C 18 alkenyl; C 2 -C 18 alkenyl which is substituted by E or interrupted by D; C 2 -C 18 alkynyl; C 2 -C 18 alkynyl which is substituted by E or interrupted by D; C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E or interrupted by D; C 4 -C 18 cycloalkyl; C 4 -C 18 cycloalkyl which is substituted by E or interrupted by D; C 4 -C 18 cycloalkenyl; or C 4 -C 18 cycloalkenyl which is substituted by E or interrupted by D;

L is E; K; C 6 -C 18 aryl or C 6 -C 18 aryl which is substituted by G, E or K;

R 4 is C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—;

R 5 and R 6 are independently of each other H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—;

or

R 5 and R 6 together form a five or six membered ring;

R 7 is H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; C 1 -C 18 alkyl which is interrupted by —O—; and

R 8 is H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; C 1 -C 18 alkyl which is interrupted by —O—.

2. A compound selected from the group consisting of C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-21, C-22, C-23, and C-24 shown below:

Cpd.

W 3

Y 3

C-2

H

H

C-3

H

H

C-4

H

H

C-5

H

H

C-6

H

H

C-7

OCH 3

OCH 3

C-8

OCH 3

OCH 3

C-9

OCH 3

OCH 3

C-10

OCH 3

OCH 3

C-11

OCH 3

OCH 3

C-12

SCH 3

SCH 3

C-13

SCH 3

SCH 3

C-14

SCH 3

SCH 3

C-15

SCH 3

SCH 3

C-16

SCH 3

SCH 3

C-17

SCH 3

SCH 3

C-18

N(CH 3 ) 2

N(CH 3 ) 2

C-19

N(CH 3 ) 2

N(CH 3 ) 2

C-20

N(CH 3 ) 2

N(CH 3 ) 2

C-21

N(CH 3 ) 2

N(CH 3 ) 2

C-22

N(CH 3 ) 2

N(CH 3 ) 2

C-23

N(CH 3 ) 2

N(CH 3 ) 2

C-24

N(CH 3 ) 2

N(CH 3 ) 2 .

3. A compound selected from the group consisting of D-1, D-2, D-3, D-4, D-5, D-6, D-7, D-8, D-9, D-10, D-11, D-12, D-13, D-14, D-15, D-16, D-17, D-18, D-19, D-20, D-21, D-22, and D-23 shown below:

Cpd.

R 101

R 102

W 3

Y 3

D-1

C 6 H 13

C 6 H 13

H

H

D-2

Bu

Bu

H

H

D-3

Et

Et

H

H

D-4

H

H

H

H

D-5

Ph

Ph

H

H

D-6

C 6 H 13

C 6 H 13

OCH 3

OCH 3

D-7

Bu

Bu

OCH 3

OCH 3

D-8

Et

Et

OCH 3

OCH 3

D-9

H

H

OCH 3

OCH 3

D-10

Ph

Ph

OCH 3

OCH 3

D-11

C 6 H 13

C 6 H 13

SCH 3

SCH 3

D-12

Bu

Bu

SCH 3

SCH 3

D-13

Et

Et

SCH 3

SCH 3

D-14

H

H

SCH 3

SCH 3

D-15

Ph

Ph

SCH 3

SCH 3

D-16

C 6 H 13

C 6 H 13

SCH 3

SCH 3

D-17

C 6 H 13

C 6 H 13

N(CH 3 ) 2

N(CH 3 ) 2

D-18

Bu

Bu

N(CH 3 ) 2

N(CH 3 ) 2

D-19

Et

Et

N(CH 3 ) 2

N(CH 3 ) 2

D-20

H

H

N(CH 3 ) 2

N(CH 3 ) 2

D-21

Ph

Ph

N(CH 3 ) 2

N(CH 3 ) 2

D-22

C 6 H 13

C 6 H 13

N(CH 3 ) 2

N(CH 3 ) 2

D-23

Bu

Bu

N(CH 3 ) 2

N(CH 3 ) 2

wherein Bu is butyl, Et is ethyl, and Ph is phenyl.

4. A compound selected from the group consisting of E-1, E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-10, E-11, E-12, E-13, E-14, E-15, E-16, E-17, E-18, E-19, E-20, E-21, E-22, E-23, E-24, E-25, E-26, E-27, E-28, E-29, E-30, E-31, E-32, E-33, E-34, and E-35 shown below:

Cpd.

Y 3

X 3

E-1

H

H

E-2

H

H

E-3

H

H

E-4

H

H

E-5

H

H

E-6

OCH 3

OCH 3

E-7

OCH 3

OCH 3

E-8

OCH 3

OCH 3

E-9

OCH 3

OCH 3

E-10

OCH 3

OCH 3

E-11

OCH 3

H

E-12

OCH 3

H

E-13

OCH 3

H

E-14

OCH 3

H

E-15

OCH 3

H

E-16

SCH 3

SCH 3

E-17

SCH 3

SCH 3

E-18

SCH 3

SCH 3

E-19

SCH 3

SCH 3

E-20

SCH 3

SCH 3

E-21

SCH 3

H

E-22

SCH 3

H

E-23

SCH 3

H

E-24

SCH 3

H

E-25

SCH 3

H

E-26

N(CH 3 ) 2

N(CH 3 ) 2

E-27

N(CH 3 ) 2

N(CH 3 ) 2

E-28

N(CH 3 ) 2

N(CH 3 ) 2

E-29

N(CH 3 ) 2

N(CH 3 ) 2

E-30

N(CH 3 ) 2

N(CH 3 ) 2

E-31

N(CH 3 ) 2

H

E-32

N(CH 3 ) 2

H

E-33

N(CH 3 ) 2

H

E-34

N(CH 3 ) 2

H

E-35

N(CH 3 ) 2

H.

5. A compound selected from the group consisting of F-1, F-2, F-3, F-4, F-5, F-6, F-7, F-8, F-9, F-10, F-11, F-12, F-13, F-14, F-15, F-16, F-17, F-18, F-19, F-20, F-21, F-22, F-23, F-24, F-25, F-26, F-27, F-28, F-29, F-30, F-31, F-32, F-33, F-34, and F-35 shown below:

Cpd.

R 101

R 102

Y 3

X 3

F-1

C 6 H 13

C 6 H 13

H

H

F-2

Bu

Bu

H

H

F-3

Et

Et

H

H

F-4

H

H

H

H

F-5

Ph

Ph

H

H

F-6

C 6 H 13

C 6 H 13

OCH 3

OCH 3

F-7

Bu

Bu

OCH 3

OCH 3

F-8

Et

Et

OCH 3

OCH 3

F-9

H

H

OCH 3

OCH 3

F-10

Ph

Ph

OCH 3

OCH 3

F-11

C 6 H 13

C 6 H 13

OCH 3

H

F-12

Bu

Bu

OCH 3

H

F-13

Et

Et

OCH 3

H

F-14

H

H

OCH 3

H

F-15

Ph

Ph

OCH 3

H

F-16

C 6 H 13

C 6 H 13

SCH 3

SCH 3

F-17

Bu

Bu

SCH 3

SCH 3

F-18

Et

Et

SCH 3

SCH 3

F-19

H

H

SCH 3

SCH 3

F-20

Ph

Ph

SCH 3

SCH 3

F-21

C 6 H 13

C 6 H 13

SCH 3

H

F-22

Bu

Bu

SCH 3

H

F-23

Et

Et

SCH 3

H

F-24

H

H

SCH 3

H

F-25

Ph

Ph

SCH 3

H

F-26

C 6 H 13

C 6 H 13

N(CH 3 ) 2

N(CH 3 ) 2

F-27

Bu

Bu

N(CH 3 ) 2

N(CH 3 ) 2

F-28

Et

Et

N(CH 3 ) 2

N(CH 3 ) 2

F-29

H

H

N(CH 3 ) 2

N(CH 3 ) 2

F-30

Ph

Ph

N(CH 3 ) 2

N(CH 3 ) 2

F-31

C 6 H 13

C 6 H 13

N(CH 3 ) 2

H

F-32

Bu

Bu

N(CH 3 ) 2

H

F-33

Et

Et

N(CH 3 ) 2

H

F-34

H

H

N(CH 3 ) 2

H

F-35

Ph

Ph

N(CH 3 ) 2

H

wherein Bu is butyl, Et is ethyl, and Ph is phenyl.

6. An electroluminescent device comprising the compound of claim 1 .

7. An electroluminescent device comprising the compound of claim 2 .

8. An electroluminescent device comprising the compound of claim 3 .

9. An electroluminescent device comprising the compound of claim 4 .

10. An electroluminescent device comprising the compound of claim 5 .

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT APPL. NO. 14/901,736 PREVIOUSLY RECORDED AT REEL: 039460 FRAME: 0615. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 8, 2017
From: BASF SE
To: UDC IRELAND LIMITED
Reel/Frame 042740/0222 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2016
From: BASF SE
To: UDC IRELAND LIMITED
Reel/Frame 039460/0615 →
Priority Claims (2)
GB 0225244.3 · Oct 30, 2002 · national
EP 03405047 · Jan 31, 2003 · regional
Continuity (4)
Continuation 12794828 · Jun 7, 2010
Continuation 10531780
Related Publication 20130079517A1 · Mar 28, 2013
Related Publication 20170194568A9 · Jul 6, 2017