Electroluminescent device
The present invention relates to an electronic device, especially an electroluminescent devices, comprising a compound of Formula (I), especially as host for phosphorescent compounds. The hosts may function with phosphorescent materials to provide improved efficiency, stability, manufacturability, or spectral characteristics of electroluminescent devices.
1. An electroluminescent (EL) device, comprising a compound of the formula
selected from the group consisting of
wherein m can be the same or different at each occurrence and is 0, 1, 2, or 3,
R 1 and R 2 are a group of formula
and
R 3 is hydrogen and R 4 is a C 1 -C 25 alkyl group, or a group of formula
or R 3 and R 4 are a group of formula
wherein R 7 , R 8 and R 9 are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, or C 1 -C 18 alkyl which is interrupted by O,
R 5 and R 6 are independently of each other halogen, or an organic substituent, or
R 5 and R 6 , which are adjacent to each other, together form an aromatic, or heteroaromatic ring, or ring system, which can optionally be substituted, and
-L 1 -X 1 and -L 2 -X 2 are independently of each other a group of formula
-NA 1 A 1′ or a group
wherein
A 1 , A 1′ , A 3 and A 3′ are independently of each other a C 6 -C 24 aryl group, or a C 2 -C 30 heteroaryl group, which can optionally be substituted, selected from the group consisting of phenyl, naphthyl, anthryl, biphenylyl, 2-fluorenyl, phenanthryl, and perylenyl, which can optionally be substituted, said groups being selected from the group consisting of
or A 1 and A 1′ , or A 3 and A 3′ together with the nitrogen atom to which they are bonded form a heteroaromatic ring, or ring system, selected from the group consisting of
wherein m′ is 0, 1, or 2;
m1 can be the same or different at each occurence and is 0, 1, 2, 3, or 4;
R 116 , R 117 and R 117′ are independently of each other H, halogen, —CN, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, —C(═O)—R 127 , —C(═O)OR 127 , or —C(═O)NR 127 R 126 , or
substituents R 116 , R 117 and R 117′ , which are adjacent to each other, can form a ring,
R 119 and R 120 are independently of each other C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, or C 7 -C 25 aralkyl, or
R 119 and R 120 together form a group of formula ═CR 121 R 122 , wherein
R 121 and R 122 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 24 aryl, C 6 -C 24 aryl which is substituted by G, or C 2 -C 20 heteroaryl, or C 2 -C 20 heteroaryl which is substituted by G, or
R 119 and R 120 together form a five or six membered ring, which optionally can be substituted by C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, or —C(═O)—R 127 ,
R 126 and R 127 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—,
BU is
wherein R 41 can be the same or different at each occurrence and is Cl, F, CN, NR 45 R 45′ , a C 1 -C 25 alkyl group, a C 4 -C 18 cycloalkyl group, a C 1 -C 25 alkoxy group, in which one or more carbon atoms which are not adjacent to each other could be replaced by —NR 45 —, —O—, —S—, —C(═O)—O—, or —O—C(═O)—O—, and/or wherein one or more hydrogen atoms can be replaced by F, a C 6 -C 24 aryl group, or a C 6 -C 24 aryloxy group, wherein one or more carbon atoms can be replaced by O, S, or N, and/or which can be substituted by one or more non-aromatic groups R 41 , or
two or more groups R 41 form a ring system;
R 45 and R 45′ are independently of each other a C 1 -C 25 alkyl group, a C 4 -C 18 cycloalkyl group, in which one or more carbon atoms which are not adjacent to each other could be replaced by —NR 45″ —, —O—, —S—, —C(═O)—O—, or, —O—C(═O)—O—, and/or wherein one or more hydrogen atoms can be replaced by F, a C 6 -C 24 aryl group, or a C 6 -C 24 aryloxy group, wherein one or more carbon atoms can be replaced by O, S, or N, and/or which can be substituted by one or more non-aromatic groups R 41 ,
R 45′ is a C 1 -C 25 alkyl group, or a C 4 -C 18 cycloalkyl group, and m1 can be the same or different at each occurrence and is 0, 1, 2, 3 or 4; or -L 1 -X 1 and -L 2 -X 2 are independently of each other a group
wherein
R 116 , R 116′ , R 117 and R 117′ are as defined above,
D is —CO—, —COO—, —S—, —SO—, —SO 2 —, —O—, —NR 65 —, —SiR 70 R 71 —, —POR 72 —, —CR 63 ═CR 64 —, or —C≡C—, and
E is −OR 69 , —SR 69 , —NR 65 R 66 , —COR 68 , —COOR 67 , —CONR 65 R 66 , —CN, or halogen,
G is E, or C 1 -C 18 alkyl; or -L 1 -X 1 and -L 2 -X 2 are independently of each other a group
wherein R 116 , R 117 and R 117′ are as defined above.
2. The EL device according to claim 1 , comprising a compound of the formula (I), wherein -L 1 -X 1 and -L 2 -X 2 are independently of each other a group of formula
-NA 1 A 1′ , or a group
wherein
A 1 , A 1′ , A 3 and A 3′ are independently of each other
or A 3 and A 3′ together with the nitrogen atom to which they are bonded form a group of formula
R 116 and R 117 are independently of each other C 1 -C 25 alkyl, which may optionally be interrupted by —O—, or C 1 -C 25 alkoxy;
Bu is
wherein R 41 can be the same or different at each occurence and is C 1 -C 25 alkyl, which may optionally be interrupted by —O—, or C 1 -C 25 alkoxy; and m1 is 0, 1, or 2.
3. The EL device according to claim 1 , comprising a compound selected from
Compound
X 1 = X 2
A1
HE-1
A2
HE-2
A3
HE-3
A4
HE-4
A5
HE-5
A6
HE-6
A7
HE-7
A8
HE-8
A9
HE-9
A10
AR-1
A11
AR-2
A12
AR-3
A13
AR-4
A14
AM-1
A15
AM-2
A17
AM-3
A18
AM-4
A19
AM-5
A20
AM-6
A21
AM-7
Compound
X 1 = X 2
B1
HE-1
B2
HE-2
B3
HE-3
B4
HE-4
B5
HE-5
B6
HE-6
B7
HE-7
B8
HE-8
B9
HE-9
B10
AR-1
B11
AR-2
B12
AR-3
B13
AR-4
B14
AM-1
B15
AM-2
B17
AM-3
B18
AM-4
B19
AM-5
B20
AM-6
B21
AM-7
Compound
X 1 = X 2
C1
HE-1
C2
HE-2
C3
HE-3
C4
HE-4
C5
HE-5
C6
HE-6
C7
HE-7
C8
HE-8
C9
HE-9
C10
AR-1
C11
AR-2
C12
AR-3
C13
AR-4
C14
AM-1
C15
AM-2
C17
AM-3
C18
AM-4
C19
AM-5
C20
AM-6
C21
AM-7
Compound
X 1 = X 2
D1
HE-1
D2
HE-2
D3
HE-3
D4
HE-4
D5
HE-5
D6
HE-6
D7
HE-7
D8
HE-8
D9
HE-9
D10
AR-1
D11
AR-2
D12
AR-3
D13
AR-4
D14
AM-1
D15
AM-2
D17
AM-3
D18
AM-4
D19
AM-5
D20
AM-6
D21
AM-7
4. The electroluminescent device according to claim 1 , comprising a cathode, an anode, and therebetween a light emitting layer containing a host material and a phosphorescent light-emitting material, wherein the host material is a compound of formula I.
5. A compound of the formula
selected from the group consisting of
wherein m can be the same or different at each occurrence and is 0, 1, 2, or 3,
R 1 and R 2 are a group of formula
and
R 3 is hydrogen and R 4 is a C 1 -C 25 alkyl group, or a group of formula
R 3 is hydrogen and R 4 is a C 1 -C 25 alkyl group, or a group of formula
or R 3 and R 4 are a group of formula
wherein R 7 , R 8 and R 9 are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, or C 1 -C 18 alkyl which is interrupted by O,
R 5 and R 6 are independently of each other halogen, or an organic substituent, or
R 5 and R 6 , which are adjacent to each other, together form an aromatic, or heteroaromatic ring, or ring system, which can optionally be substituted, and
-L 1 -X 1 and -L 2 -X 2 are independently of each other a group of formula
-NA 1 A 1′ , or a group
wherein
A 1 , A 1′ , A 3 and A 3′ are independently of each other a C 6 -C 24 aryl group, or a C 2 -C 30 heteroaryl group, which can optionally be substituted, selected from the group consisting of phenyl, naphthyl, anthryl, biphenylyl, 2-fluorenyl, phenanthryl, and perylenyl, which can optionally be substituted, said groups being selected from the group consisting
of
or A 1 and A 1′ , or A 3 and A 3′ together with the nitrogen atom to which they are bonded form a heteroaromatic ring, or ring system, selected from the group consisting
of
of wherein m′ is 0, 1, or 2;
m1 can be the same or different at each occurrence and is 0, 1, 2, 3, or 4;
R 116 , R 117 and R 117′ are independently of each other H, halogen, —CN, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, —C(═O)—R 127 , —C(═O)OR 127 , or —C(═O)NR 127 R 126 , or
substituents R 116 , R 117 and R 117′ , which are adjacent to each other, can form a ring,
R 119 and R 120 are independently of each other C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, or C 7 -C 25 aralkyl, or
R 119 and R 120 together form a group of formula ═CR 121 R 122 , wherein
R 121 and R 122 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 24 aryl, C 6 -C 24 aryl which is substituted by G, or C 2 -C 20 heteroaryl, or C 2 -C 20 heteroaryl which is substituted by G, or
R 119 and R 120 together form a five or six membered ring, which optionally can be substituted by C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, or —C(═O)—R 127 ,
R 126 and R 127 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—,
BU is
wherein R 41 can be the same or different at each occurrence and is Cl, F, CN, NR 45 R 45′ , a C 1 -C 25 alkyl group, a C 4 -C 18 cycloalkyl group, a C 1 -C 25 alkoxy group, in which one or more carbon atoms which are not adjacent to each other could be replaced by —NR 45 —, —O—, —S—, or —O—C(═O)—O—, and/or wherein one or more hydrogen atoms can be replaced by F, a C 6 -C 24 aryl group, or a C 6 -C 24 aryloxy group, wherein one or more carbon atoms can be replaced by O, S, or N, and/or which can be substituted by one or more non-aromatic groups R 41 , or
two or more groups R 41 form a ring system;
R 45 and R 45′ are independently of each other a C 1 -C 25 alkyl group, a C 4 -C 18 cycloalkyl group, in which one or more carbon atoms which are not adjacent to each other could be replaced by —NR 45″ —, —O—, —S—, —C(═O)—O—, or, —O—C(═O)—O—, and/or wherein one or more hydrogen atoms can be replaced by F, a C 6 -C 24 aryl group, or a C 6 -C 24 aryloxy group, wherein one or more carbon atoms can be replaced by O, S, or N, and/or which can be substituted by one or more non-aromatic groups R 41 ,
R 45″ is a C 1 -C 25 alkyl group, or a C 4 -C 18 cycloalkyl group, and m1 can be the same or different at each occurrence and is 0, 1, 2, 3 or 4; or -L 1 -X 1 and -L 2 -X 2 are independently of each other a group
wherein
R 116 , R 116′ , R 117 and R 117′ are as defined above,
D is —CO—, —COO—, —S—, —SO—, —SO 2 —, —O—, —NR 65 —, —SiR 70 R 71 , —POR 72 —, —CR 63 ═CR 64 —, or —C≡C—, and
E is —OR 69 , —SR 69 , —NR 65 R 66 , —COR 68 , —COOR 67 , —CONR 65 R 66 , —CN, or halogen,
G is E, or C 1 -C 18 alkyl; or -L 1 -X 1 and -L 2 -X 2 are independently of each other a group
wherein R 116 , R 117 and R 117′ are as defined above.
6. A process for the preparation of compounds of the formula I according to claim 5 , wherein X 1 and X 2 are independently of each other —NA 1 A 1′ ,
m′ is 0, 1, or 2; which comprises reacting a compound of formula
wherein X 10 stands for a halogen, selected from the group consisting of bromo, and iodo,
with a compound of formula HNA 1 A 1′ ,
in the presence of a base and a catalyst in a solvent,
wherein A 1 and A 1′ are independently of each other a C 6 -C 24 aryl group, a C 2 -C 30 heteroaryl group, which can optionally be substituted, or A 1 and A 1′ together with the nitrogen atom to which they are bonded from a heteroaromatic ring, or ring system selected from the group consisting of
wherein m′ is 0, 1, or 2;
m1 can be the same or different at each occurrence and is 0, 1, 2, 3, or 4,
R 41 can be the same or different at each occurrence and is Cl, F, CN, NR 45 R 45′ , a C 1 -C 23 alkyl group, a C 4 -C 18 cycloalkyl group, a C 1 -C 25 alkoxy group, in which one or more carbon atoms which are not in neighborhood to each other could be replaced by —NR 45 —, —O—, —S—, —C(═O)—O—, or —O—C(═O)—O—, and/or wherein one or more hydrogen atoms can be replaced by F, a C 6 -C 24 aryl group, or a C 6 -C 24 aryloxy group, wherein one or more carbon atoms can be replaced by O, S, or N, and/or which can be substituted by one or more non-aromatic groups R 41 , or
two or more groups R 41 form a ring system;
R 45 and R 45′ are independently of each other a C 1 -C 25 alkyl group, a C 4 -C 18 cycloalkyl group, in which one or more carbon atoms which are not in neighborhood to each other could be replaced by —NR 45″ —, —O—, —S—, —C(═O)—O—, or, —O—C(═O)—O—, and/or wherein one or more hydrogen atoms can be replaced by F, a C 6 -C 24 aryl group, or a C 6 -C 24 aryloxy group, wherein one or more carbon atoms can be replaced by O, S, or N and/or which can be substituted by one or more non-aromatic groups R 41 , and
R 45″ is a C 1 -C 25 alkyl group, or a C 4 -C 18 cycloalkyl group.