Electroluminescent device
Disclosed are electroluminescent devices that comprise organic layers that contain dibenzofuran compounds. The compounds are suitable components of, for example, 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.
1. An electroluminescent device, comprising in the light emitting layer a compound of the formula
and a phosphorescent metal complex of Ir, Pt, Eu, Ru, Rh, Pd, Ag, Re, Os and Au as dopant, wherein R 81 and R 88 are independently of each other H, —OR 201 , —SR 202 and/or —NR 203 R 204 , C 1 -C 24 alkyl; C 1 -C 24 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, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl, which is substituted by G, aryl, aryl, which is substituted by G, heteroaryl, or heteroaryl, which is substituted by G, silyl, SiR 62 R 63 R 64 , —CN, cyclic ether, —B(OR 65 ) 2 and/or halogen, wherein
R 201 is hydrogen, C 1 -C 24 alkyl, C 1 -C 24 alkyl, which is substituted by E and/or interrupted by D; C 2 -C 12 alkenyl, C 3 -C 6 alkenoyl, C 3 -C 8 cycloalkyl, or benzoyl, each of which may optionally be substituted by one or more groups C 1 -C 6 alkyl, halogen, —OH and/or C 1 -C 4 alkoxy; phenyl, naphthyl, phenanthryl, anthranyl, or pyrenyl, each of which may optionally be substituted by halogen, —OH, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, phenoxy, C 1 -C 12 alkylsulfanyl, phenylsulfanyl, —N(C 1 -C 12 alkyl) 2 and/or diphenylamino;
R 202 is C 1 -C 24 alkyl, C 1 -C 24 alkyl, which is substituted by E and/or interrupted by D; C 2 -C 12 alkenyl, C 1 -C 8 alkanoyl, C 2 -C 12 alkenyl, C 3 -C 6 alkenoyl; C 3 -C 8 cycloalkyl, or benzoyl, each of which may optionally be substituted by one or more groups C 1 -C 6 alkyl, halogen, —OH, C 1 -C 4 alkoxy or C 1 -C 4 alkylsulfanyl; phenyl, naphthyl, phenanthryl, anthranyl, or pyrenyl, each of which may optionally be substituted by halogen, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, phenyl-C 1 -C 3 alkyloxy, phenoxy, C 1 -C 12 alkylsulfanyl, phenylsulfanyl, —N(C 1 -C 12 alkyl) 2 , diphenylamino, —(CO)O(C 1 -C 8 alkyl), —(CO)—C 1 -C 8 alkyl, or (CO)N(C 1 -C 8 alkyl) 2 ;
R 203 and R 204 are independently of each other hydrogen, C 1 -C 24 alkyl, C 1 -C 24 alkyl, which is substituted by E and/or interrupted by D; C 2 -C 2 alkenyl, C 3 -C 8 cycloalkyl, or benzoyl, each of which may optionally be substituted by one or more groups C 1 -C 6 alkyl, halogen, —OH, or C 1 -C 4 alkoxy; phenyl-C 1 -C 3 alkyl, C 1 -C 8 alkanoyl, C 3 -C 12 alkenoyl; phenyl naphthyl, phenanthryl, anthranyl, or pyrenyl, each of which is optionally substituted by C 1 -C 12 alkyl, benzoyl or C 1 -C 12 alkoxy; or R 203 and R 204 together are C 2 -C 8 alkylene, or branched C 2 -C 8 alkylene optionally interrupted by —O—, —S—, or —NR 205 — and/or optionally substituted by hydroxyl, C 1 -C 4 alkoxy, C 2 -C 4 alkanoyloxy, or benzoyloxy, wherein the ring formed by R 203 and R 204 can optionally be condensed one or two times by phenyl which can be substituted one to three times with C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen, or cyano;
R 205 is hydrogen, C 1 -C 24 alkyl, C 1 -C 24 alkyl, which is substituted by E and/or interrupted by D; C 2 -C 5 alkenyl, C 3 -C 8 cycloalkyl, phenyl-C 1 -C 3 alkyl, C 1 -C 8 alkanoyl, C 3 -C 12 alkenoyl; benzoyl; phenyl, naphthyl, phenanthryl, anthranyl, or pyrenyl, each of which is optionally substituted by C 1 -C 12 alkyl, benzoyl, or C 1 -C 12 alkoxy;
D is —CO—, —COO—, —OCOO—, —S—, —SO—, —SO 2 —, —O—, —NR 5 —, —SiR 61 R 62 —, —POR 5 —, —CR 63 ═CR 64 —, or —C≡—;
E is halogen, C 6 -C 14 aryl, which may be substituted by —OR 5 , —SR 5 , —NR 5 R 6 , SiR 62′ R 63′ R 64′ , wherein R 62′ , R 63′ and R 64′ are independently of each other a C 1 -C 8 alkyl group, a C 6 -C 24 aryl group or a C 7 -C 12 aralkyl group, —CN, cyclic ether and/or —B(OR 65 ) 2 , wherein R 65 is hydrogen, C 1 -C 24 alkyl, C 3 -C 8 cycloalkyl, C 7 -C 24 aralkyl, C 2 -C 18 alkenyl, C 2 -C 24 alkynyl, hydroxy, mercapto, C 1 -C 24 alkoxy, C 1 -C 24 alkylthio, C 6 -C 30 aryl, C 2 -C 30 heteroaryl, halogen, haloalkane, silyl, siloxanyl, and an alicyclic ring formed with adjacent substituents R 65 ; —OR 5 , —SR 5 , —NR 5 R 6 , —COR 8 , —COOR 7 , —CONR 5 R 6 , —CN, halogen, silyl, C 1 -C 18 alkyl, or heteroaryl,
G is E, or C 1 -C 18 alkyl, wherein 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, C 1 -C 18 alkoxy, or silyl; 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 7 -C 12 alkylaryl, which are optionally 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 8 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, C 7 -C 12 alkylaryl, or C 1 -C 18 alkyl which is interrupted by —O—;
R 61 and R 62 are independently of each other C 6 -C 18 aryl; C 6-18 aryl which is substituted by C 1 -C 18 alkyl, C 1 -C 18 alkoxy; or C 1 -C 18 alkyl which is interrupted by —O—,
R 63 and R 64 are independently of each other H, C 6 -C 18 aryl; C 6-18 aryl which is substituted by C 1 -C 18 alkyl, C 1 -C 18 alkoxy; or C 1 -C 18 alkyl which is interrupted by —O—,
wherein
R 82 , R 83 , R 86 and R 87 are independently of each other a group of the formula —(W 1 ) a —(W 2 ) b —W 3 ,
a and b are 0, or 1,
W 1 and W 2 are independently of each other a group of formula
and
R 11 , R 11′ , R 12 , R 12′ , R 13 , R 13′ , R 15 , R 15′ , R 16 , R 16′ , R 17 and R 17′ are independently of each other H, E, tri(C 1 -C 8 alkyl)silyl, 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 1 -C 18 alkoxy; or C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D; C 7 -C 18 aralkyl; or C 7 -C 18 aralkyl which is substituted by G;
R 18 and R 19 are independently of each other C 1 -C 18 alkyl; C 1 -C 18 alkoxy, C 6 -C 18 aryl; C 7 -C 18 aralkyl; or R 18 and R 19 together form a ring, which can optionally be substituted by C 1 -C 8 alkyl,
W 3 is a group of formula —NR 70 R 71 , wherein R 70 and R 71 are independently of each other a group of formula
wherein R 72 , R 73 and R 74 are independently of each other hydrogen, C 1 -C 8 alkyl, a hydroxyl group, a mercapto group, C 1 -C 8 alkoxy, C 1 -C 8 alkylthio, halogen, halo-C 1 -C 8 alkyl, a cyano group, an aldehyde group, a ketone group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group, or R 70 and R 71 together with the nitrogen atom to which they are bonded form a five or six membered heterocyclic ring, which can be condensed by one or two optionally substituted phenyl groups; with the proviso that b is 1, if R 70 and R 71 are independently of each other a group of formula
2. The electroluminescent device according to claim 1 , wherein the light emitting layer comprises a compound of formula
wherein R 81 , R 83 , R 86 and R 88 are as defined in claim 1 .
3. The electroluminescent device according to claim 1 , wherein the light emitting layer comprises a compound of formula
wherein
R 81 and R 83 are independently of each other H, or NR 203 R 204 ,
R 203 and R 204 together form a five membered ring, wherein the ring formed by R 203 and R 204 can optionally be condensed one or two times by phenyl;
R 86 and R 88 are independently of each other a group of the formula —(W 1 ) a —(W 2 ) b —W 3 ,
a and b are 0, or 1,
W 1 and W 2 are independently of each other a group of formula
R 11 , R 11′ , R 12 and R 12′ R are H; and
W 3 is a group of formula —NR 70 R 71 , wherein R 70 and R 71 together with the nitrogen atom to which they are bonded form a five or six membered heterocyclic ring, which can be condensed by one or two optionally substituted phenyl groups.
4. The electroluminescent device according to claim 1 , wherein the compound of formula (Ia) is a compound of formula
5. A method of forming a light emitting layer of an electroluminescent device by incorporating the compounds of formula (Ia), (Ib), or (Ic) according to claim 1 with phosphorescent metal complexes of Ir, Pt, Eu, Ru, Rh, Pd, Ag, Re, Os and Au as a dopant therein.