IP Library › Patent Application 12794828

Patent Application

App. No. 12/794,828

ELECTROLUMINESCENT DEVICE

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Patent No.: US None
App. No.: 12/794,828

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Abstract

Disclosed are electroluminescent devices that comprise organic layers that contain certain organic compounds containing one ore more pyrimidine moieties. The organic compounds containing one ore 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 (107)

1 . A pyrimidine compound of formula (I)

wherein V is

H; C r C 1-18 alkyl; C 1 -C 18 alkyl 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 ;

W is

Y is

X is

V 1 to V 5 , W 1 to W 5 , X 1 to X 5 and Y 1 to Y 5 are independently of each other H; halogen;

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;

wherein Ar 1 is C 6 -C 30 aryl or C 2 -C 30 heteroaryl and Ar 2 is C 6 -C 30 aryl or C 2 -C 18 heteroaryl; 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 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;

W 5 or Y 5 together with V form a group —CR 9 2 —, —CR 9 2 —CR 9 2 , —C(═O)CR 9 2 , —C(═O)— or —CR 9 ═CR 9 —, or

W 5 and Y 5 together with V form a group

wherein R 9 is H; C 1 -C 18 alkyl; C 1 -C 18 alkyl which is interrupted by —O—; 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, or

one of the substituents V, W, X or Y is a group of the formula —Z;

wherein Z is a group of formula

one of the substituents

V 1 to V 5 , W 1 to W 5 , X 1 to X 5 , or Y 1 to Y 5 is a group of the formula —Z′;

wherein Z′ is a group of formula

wherein

A 1 , B 1 and B 2 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; or

two substituents A 1 , B 1 , B 2 or B 1 and B 2 form a five to seven membered ring, which can be substituted,

m is an integer of 1 to 4; and W 1 , W 2 , Y 1 , Y 2 , X 1 , X 2 , V, W, X and Y are as defined above;

D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO 2 —; —O—; —NR S —; —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 and/or K;

K is 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 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; 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; or C 4 -C 18 cycloalkenyl which is substituted by E and/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 and/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 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 m 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 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—;

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—;

or two substituents selected from V 1 to V 5 , W 1 to W 5 , X 1 to X 5 , Y 1 to Y 5 which are in neighborhood to each other form a five to seven membered ring, with the proviso that at least one of the groups V, W, X and Y is a group

2 . A pyrimidine compound according to claim 1 or formula (III)

wherein

Y is R 1 , if X is

or X is R 1 , if Y is

R 1 is H; C 1 -C 18 alkyl; C 1 -C 18 alkyl 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 ; or

—NR 5 R 6 ; wherein W 1 to W 5 , X 1 to X 5 , Y 1 to Y 5 , E, D, R 5 and R 6 are as defined in claim 1 and V is H.

3 . A pyrimidine compound according to claim 1 of formula (IV)

wherein

V, W 1 to W 5 , X 1 to X 5 and Y 1 to Y 5 are as defined in claim 1 ; W 3 , X 3 and Y 3 are selected from the group consisting of C 6 -C 24 aryl; C 6 -C 24 aryl which is substituted by G; C 2 -C 24 heteroaryl; C 2 -C 24 heteroaryl which is substituted by L; C 1 -C 18 alkoxy; —SR 5 or

—NR 5 R 6 , wherein G, L, R 5 and R 6 are as defined in claim 1 ,

V is H, and W 1 and W 5 , Y 1 and Y 5 as well as X 1 and X 5 are independently of each other H; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, wherein E and D are as defined in claim 1 .

4 . A pyrimidine compound according to claim 1 , wherein V is a group of the formula

H; C 1 -C 18 alkyl; C 1 -C 18 alkyl 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 ; or

—NR 5 R 6 ; and W is a group of the formula

H; C 1 -C 18 alkyl; C 1 -C 18 alkyl 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 ; or -NR 5 R 6 ; wherein W 1 to W 5 , D, V 1 to V 5 , E, A 1 , B 1 , B 2 , R 5 , R 6 , m and Z are as defined in claim 1 and R 101 and R 102 are independently of each other H;

C 1 -C 8 alkyl; C 6 -C 24 aryl or C 5 -C 7 cycloalkyl.

5 . A pyrimidine compound according to claim 1 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 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 8 ; —COOR 7 ; 213 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; 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 ; or —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 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;

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; wherein D, E, G, L, R 4 , R 5 , R 6 , R 7 and R 8 are as defined in claim 1 .

6 . A pyrimidine compound according to claim 1 of formula (Xa) or (Xb)

wherein V is H or C 1 -C 8 -alkyl;

X 3 and X 4 are independently of each other H; C 1 -C 8 alkyl; C 1 -C 8 alkoxy; C 1 -C 8 thioalkyl or phenyl;

X 5 is H or C 1 -C 8 alkoxy;

W 5 is H; C 1 -C 8 alkyl or O(CH 2 ) n1 —X;

Y 5 is H; C 1 -C 8 alkyl or O(CH 2 ) n1 —X;

Y 3 , Y 4 , W 3 andW 4 are independently of each other C 1 -C 8 alkyl; C 1 -C 8 alkoxy; C 1 -C 8 thioalkyl; halogen; phenyl; or O(CH 2 ) n1 —X, wherein n1 is an integer of 1 to 5 and X is —O—(CH 2 ) m1 CH 3 ; —OC(O)—(CH 2 ) m1 CH 3 ; —C(O)—O—C 1 -C 8 alkyl or —NR 103 R 104 ; wherein m1 is an integer of 0 to 5 and R 103 and R 104 are independently of each other H or C 1 -C 8 -alkyl, or R 103 and R 104 together form a five or six membered heterocyclic ring;

or of formula (XI)

wherein V is H or C 1 -C 8 alkyl;

W 3 is H; C 1 -C 8 alkyl or C 1 -C 8 alkoxy;

X 3 is H; C 1 -C 8 alkoxy; phenyl or O(CH 2 ) n1 —X;

X 5 is H; C 1 -C 8 alkoxy; phenyl or O(CH 2 ) n1 —X;

Y 3 is H; C 1 -C 8 alkyl or C 1 -C 8 alkoxy, wherein n1 is an integer of 1 to 4 and X is —O—(CH 2 ) m1 CH 3 ; —OC(O)—(CH 2 ) m1 CH 3 ; or —C(O)—O—C 1 C 8 alkyl, wherein m1 is an integer of 0 to 5;

or of formula (XIIa) or (XIIb)

wherein W 3 and W 4 are independently of each other H; —NR 103 R 104 ; C 1 -C 8 thioalkyl or C 1 -C 8 alkoxy;

Y 3 and Y 4 are independently of each other H; —NR 103 R 104 ; C 1 -C 8 thioalkyl or C 1 -C 8 alkoxy;

wherein R 103 and R 104 are independently of each other H or C 1 -C 8 alkyl;

W 5 is H; C 1 -C 8 alkyl or O(CH 2 ) m1 —X;

Y 5 is H; C 1 -C 8 alkyl; or O(CH 2 ) n1 —X;

wherein n1 is an integer of 1 to 5 and X is —O—(CH 2 ) m1 CH 3 ; —O—C(O)—(CH 2 ) m1 CH 3 ;

—C(O)—O—C 1 -C 8 alkyl or —NR 103 R 104 , wherein m1 is an integer of 0 to 5 and R 103 and R 104 are independently of each other H or C 1 -C 8 -alkyl, or R 103 and R 104 together form a five or six membered heterocyclic ring;

or of formula (XV)

wherein W 3 is H; —NR 103 R 104 ; C 1 -C 8 thioalkyl or C 1 -C 8 alkoxy;

Y 3 is H; —NR 103 R 104 ; C 1 -C 8 thioalkyl or C 1 -C 8 alkoxy, wherein R 103 and R 104 are independently of each other H or C 1 -C 8 alkyl;

R 101 and R 102 are independently of each other H; C 1 -C 8 alkyl; phenyl or C 5 -C 7 cycloalkyl;

or of formula (XVI)

wherein Y 3 is H; —NR 103 R 104 ; C 1 -C 8 thioalkyl or C 1 -C 8 alkoxy;

X 3 is H; —NR 103 R 104 ; C 1 -C 8 thioalkyl or C 1 -C 8 alkoxy, wherein R 103 and R 104 are independently of each other H or C 1 -C 8 alkyl;

or of formula (XVII)

wherein

Y 3 is H; —NR 103 R 104 ;C 1 -C 8 thioalkyl or C 1 -C 8 alkoxy;

X 3 is H; —NR 103 R 104 ; C 8 thioalkyl or C 1 -C 8 alkoxy, wherein R 103 and R 104 are independently of each other H or C 1 -C 8 alkyl, and R 101 and R 102 are independently of each other H; C 1 -C 8 alkyl; phenyl or C 5 -C 7 cycloalkyl.

7 . A pyrimidine compound according to claim 1 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 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;

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;

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 8 -C 18 aryl which is substituted by E; and

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 alkm; 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 ; or —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; wherein D, E, G, L, R 4 , R 5 , R 6 , R 7 and R 8 are as defined in claim 1 .