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US 8,946,984 B2Granted
Electroluminescent device
AssigneeBASF SE
InventorsJunichi Tanabe, Hidetaka Oka, Hiroshi Yamamoto
Life of this patent
Estimating the term…
Abstract
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.
Claims5
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 R81 and R88 are independently of each other H, —OR201, —SR202 and/or —NR203R204, C1-C24alkyl;
- C1-C24alkyl, which is substituted by E and/or interrupted by D;
- C2-C18alkenyl, C2-C18alkenyl, which is substituted by E, C3-C8cycloalkyl, C3-C8cycloalkyl, which is substituted by G, aryl, aryl, which is substituted by G, heteroaryl, or heteroaryl, which is substituted by G, silyl, SiR62R63R64, —CN, cyclic ether, —B(OR65)2 and/or halogen, wherein
- R201 is hydrogen, C1-C24alkyl, C1-C24alkyl, which is substituted by E and/or interrupted by D;
- C2-C12alkenyl, C3-C6alkenoyl, C3-C8cycloalkyl, or benzoyl, each of which may optionally be substituted by one or more groups C1-C6alkyl, halogen, —OH and/or C1-C4alkoxy;
- phenyl, naphthyl, phenanthryl, anthranyl, or pyrenyl, each of which may optionally be substituted by halogen, —OH, C1-C12alkyl, C1-C12alkoxy, phenoxy, C1-C12alkylsulfanyl, phenylsulfanyl, —N(C1-C12alkyl)2 and/or diphenylamino;
- R202 is C1-C24alkyl, C1-C24alkyl, which is substituted by E and/or interrupted by D;
- C2-C12alkenyl, C1-C8alkanoyl, C2-C12alkenyl, C3-C6alkenoyl;
- C3-C8cycloalkyl, or benzoyl, each of which may optionally be substituted by one or more groups C1-C6alkyl, halogen, —OH, C1-C4alkoxy or C1-C4alkylsulfanyl;
- phenyl, naphthyl, phenanthryl, anthranyl, or pyrenyl, each of which may optionally be substituted by halogen, C1-C12alkyl, C1-C12alkoxy, phenyl-C1-C3alkyloxy, phenoxy, C1-C12alkylsulfanyl, phenylsulfanyl, —N(C1-C12alkyl)2, diphenylamino, —(CO)O(C1-C8alkyl), —(CO)—C1-C8alkyl, or (CO)N(C1-C8alkyl)2;
- R203 and R204 are independently of each other hydrogen, C1-C24alkyl, C1-C24alkyl, which is substituted by E and/or interrupted by D;
- C2-C2alkenyl, C3-C8cycloalkyl, or benzoyl, each of which may optionally be substituted by one or more groups C1-C6alkyl, halogen, —OH, or C1-C4alkoxy;
- phenyl-C1-C3alkyl, C1-C8alkanoyl, C3-C12alkenoyl;
- phenyl naphthyl, phenanthryl, anthranyl, or pyrenyl, each of which is optionally substituted by C1-C12alkyl, benzoyl or C1-C12alkoxy;
- or R203 and R204 together are C2-C8alkylene, or branched C2-C8alkylene optionally interrupted by —O—, —S—, or —NR205— and/or optionally substituted by hydroxyl, C1-C4alkoxy, C2-C4alkanoyloxy, or benzoyloxy, wherein the ring formed by R203 and R204 can optionally be condensed one or two times by phenyl which can be substituted one to three times with C1-C8-alkyl, C1-C8-alkoxy, halogen, or cyano;
- R205 is hydrogen, C1-C24alkyl, C1-C24alkyl, which is substituted by E and/or interrupted by D;
- C2-C5alkenyl, C3-C8cycloalkyl, phenyl-C1-C3alkyl, C1-C8alkanoyl, C3-C12alkenoyl;
- benzoyl;
- phenyl, naphthyl, phenanthryl, anthranyl, or pyrenyl, each of which is optionally substituted by C1-C12alkyl, benzoyl, or C1-C12alkoxy;
- D is —CO—, —COO—, —OCOO—, —S—, —SO—, —SO2—, —O—, —NR5—, —SiR61R62—, —POR5—, —CR63═CR64—, or —C≡—;
- E is halogen, C6-C14aryl, which may be substituted by —OR5, —SR5, —NR5R6, SiR62′R63′R64′, wherein R62′, R63′ and R64′ are independently of each other a C1-C8alkyl group, a C6-C24aryl group or a C7-C12aralkyl group, —CN, cyclic ether and/or —B(OR65)2, wherein R65 is hydrogen, C1-C24alkyl, C3-C8cycloalkyl, C7-C24aralkyl, C2-C18alkenyl, C2-C24alkynyl, hydroxy, mercapto, C1-C24alkoxy, C1-C24alkylthio, C6-C30aryl, C2-C30heteroaryl, halogen, haloalkane, silyl, siloxanyl, and an alicyclic ring formed with adjacent substituents R65;
- —OR5, —SR5, —NR5R6, —COR8, —COOR7, —CONR5R6, —CN, halogen, silyl, C1-C18alkyl, or heteroaryl,
- G is E, or C1-C18alkyl, wherein R5 and R6 are independently of each other H, C6-C18aryl;
- C6-C18aryl which is substituted by C1-C18alkyl, C1-C18alkoxy, or silyl;
- C1-C18alkyl or C1-C18alkyl which is interrupted by —O—;
- or
- R5 and R6 together form a five or six membered ring,
- R7 is H, C6-C18aryl, C7-C12alkylaryl, which are optionally substituted by C1-C18alkyl, or C1-C18alkoxy;
- C1-C18alkyl;
- or C1-C18alkyl which is interrupted by —O—;
- R8 is C6-C18aryl;
- C6-C18aryl which is substituted by C1-C18alkyl, or C1-C18alkoxy;
- C1-C18alkyl, C7-C12alkylaryl, or C1-C18alkyl which is interrupted by —O—;
- R61 and R62 are independently of each other C6-C18aryl;
- C6-18aryl which is substituted by C1-C18alkyl, C1-C18alkoxy;
- or C1-C18alkyl which is interrupted by —O—,
- R63 and R64 are independently of each other H, C6-C18aryl;
- C6-18aryl which is substituted by C1-C18alkyl, C1-C18alkoxy;
- or C1-C18alkyl which is interrupted by —O—,
- wherein
- R82, R83, R86 and R87 are independently of each other a group of the formula —(W1)a—(W2)b—W3,
- a and b are 0, or 1,
- W1 and W2 are independently of each other a group of formula
- and
- R11, R11′, R12, R12′, R13, R13′, R15, R15′, R16, R16′, R17 and R17′ are independently of each other H, E, tri(C1-C8alkyl)silyl, C6-C18aryl;
- C6-C18aryl which is substituted by G;
- C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C1-C18alkoxy;
- or C1-C18alkoxy which is substituted by E and/or interrupted by D;
- C7-C18aralkyl;
- or C7-C18aralkyl which is substituted by G;
- R18 and R19 are independently of each other C1-C18alkyl;
- C1-C18alkoxy, C6-C18aryl;
- C7-C18aralkyl;
- or R18 and R19 together form a ring, which can optionally be substituted by C1-C8alkyl,
- W3 is a group of formula —NR70R71, wherein R70 and R71 are independently of each other a group of formula
- wherein R72, R73 and R74 are independently of each other hydrogen, C1-C8alkyl, a hydroxyl group, a mercapto group, C1-C8alkoxy, C1-C8alkylthio, halogen, halo-C1-C8alkyl, 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 R70 and R71 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 R70 and R71 are independently of each other a group of formula
56 more elements
Dependencies are inferred from the claim text.