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US 2006/0041126 A1Published application
Electroluminescent device
AssigneeCiba Specialty Chemicals Holding Inc.
InventorsThomas Schafer, Patrice Bujard, Jonathan Rogers, Kristina Bardon
Life of this patent
Estimating the term…
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.
Claims21
An electroluminescent device comprising an anode, a cathode and one or a plurality of organic compound layers sandwiched therebetween, in which said organic compound layers comprise an organic compound containing one ore more pyrimidine moieties.
(canceled)
An electroluminescent device according to claim 18, comprising a pyrimidine compound of formula
- Y is R1, if X is
- or X is R1, if Y is
- R1 is H, C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C2-C18alkenyl, C2-C18alkenyl which is substituted by E and/or interrupted by D;
- C2-C18alkynyl;
- C2-C18alkynyl which is substituted by E and/or interrupted by D;
- C1-C18alkoxy;
- C1-C18alkoxy which is substituted by E and/or interrupted by D;
- —SR5;
- or —NR5R6;
- and V is H.
9 more elements
An electroluminescent device according to claim 18, comprising a pyrimidine compound of formula
- wherein
- V is H, and W1 and W5, Y1 and Y5 as well as X1 and X5 are independently of each other H;
- C1-C18alkyl;
- or C1-C18alkyl which is substituted by E and/or interrupted by D.
1 more element
An electroluminescent device according to claim 18, wherein V is a group of the formula
- H, C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C2-C18alkenyl, C2-C18alkenyl which is substituted by E and/or interrupted by D;
- C2-C18alkynyl;
- C2-C18alkynyl which is substituted by E and/or interrupted by D;
- C1-C18alkoxy;
- C1-C18alkoxy which is substituted by E and/or interrupted by D;
- —SR5;
- or —NR5R6;
- and
- W is a group of the formula
- H, C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C2-C18alkenyl, C2-C18alkenyl which is substituted by E and/or interrupted by D;
- C2-C18alkynyl;
- C2-C18alkynyl which is substituted by E and/or interrupted by D;
- C1-C18alkoxy;
- C1-C18alkoxy which is substituted by E and/or interrupted by D;
- —SR5;
- or —NR5R6;
- and R101 and R102 are independently of each other H, C1-C8alkyl, C6-C24aryl, or C5-C7cycloalkyl.
18 more elements
An electroluminescent device according to claim 17, comprising a pyrimidine compound of formula
- wherein
- Ar is a group of formula
- W11 to W15, W21 to W25, W31 to W35, W41 to W45, Y11 to Y15, Y21 to Y25, Y31 to Y35 and to Y45 are independently of each other H;
- C6-C24aryl;
- C6-C24aryl which is substituted by G;
- C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C7-C18alkylaryl;
- C7-C18alkylaryl which is substituted by E and/or interrupted by D;
- C2-C18alkenyl;
- C2-C18alkenyl which is substituted by E and/or interrupted by D;
- C2-C18alkynyl;
- C2-C18alkynyl which is substituted by E and/or interrupted by D;
- C1-C18alkoxy, C1-C18alkoxy which is substituted by E and/or interrupted by D;
- —SR5;
- —NR5R6;
- C2-C24heteroaryl;
- C2-C24heteroaryl which is substituted by L;
- —SOR4;
- —SO2R4;
- —COR8;
- —COOR7;
- —CONR5R6;
- C4-C18cycloalkyl;
- C4-C18cycloalkyl which is substituted by E and/or interrupted by D;
- C4-C18cycloalkenyl;
- C4-C18cycloalkenyl which is substituted by E and/or interrupted by D;
- V is H;
- C6-C24aryl;
- C6-C24aryl which is substituted by G;
- C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C7-C18alkylaryl;
- C7-C18alkylaryl which is substituted by E and/or interrupted by D;
- C2-C18alkenyl;
- C2-C18alkenyl which is substituted by E and/or interrupted by D;
- C2-C18alkynyl;
- C2-C18alkynyl which is substituted by E and/or interrupted by D;
- C1-C18alkoxy, C1-C18alkoxy which is substituted by E and/or interrupted by D;
- —SR5;
- or —NR5R6;
- C2-C24heteroaryl;
- C2-C24heteroaryl which is substituted by L;
- —SOR4;
- —SO2R4;
- —COR8;
- —COOR7;
- —CONR5R6;
- C4-C18cycloalkyl;
- C4-C18cycloalkyl which is substituted by E and/or interrupted by D;
- C4-C18cycloalkenyl;
- C4-C18cycloalkenyl which is substituted by E and/or interrupted by D;
- A18 and A19 are independently of each other H, C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C6-C18aryl;
- C6-C18aryl which is substituted by E, B11 to B14 and B21 to B24 are independently of each other H;
- C6-C18aryl;
- C6-C18aryl which is substituted by G;
- C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C7-C18alkylaryl;
- C7-C18alkylaryl which is substituted by E and/or interrupted by D;
- C2-C18alkenyl;
- C2-C18alkenyl which is substituted by E and/or interrupted by D;
- C2-C18alkynyl;
- C2-C18alkynyl which is substituted by E and/or interrupted by D;
- C1-C18alkoxy, C1-C18alkoxy which is substituted by E and/or interrupted by D;
- —SR5;
- —NR5R6;
- C2-C18heteroaryl;
- C2-C18heteroaryl which is substituted by L;
- —SOR4;
- —SO2R4;
- —COR8;
- —COOR7;
- or —CONR5R6;
- C4-C18cycloalkyl;
- C4-C18cycloalkyl which is substituted by E and/or interrupted by D;
- C4-C18cycloalkenyl;
- C4-C18cycloalkenyl which is substituted by E and/or interrupted by D.
- G is E;
- K;
- heteroaryl;
- heteroaryl which is substituted by C6-C18aryl;
- C6-C18aryl which is substituted by E and/or K;
- K is C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C7-C18alkylaryl which is substituted by E and/or interrupted by D;
- C2-C18alkenyl;
- C2-C18alkenyl which is substituted by E and/or interrupted by D;
- C2-C18alkynyl;
- C2-C18alkynyl which is substituted by E and/or interrupted by D:
- C1-C18alkoxy. C1-C18alkoxy which is substituted by E and/or interrupted by D;
- C4-C18cycloalkyl;
- C4-C18cycloalkyl which is substituted by E and/or interrupted by D:
- C4-C18cycloalkenyl;
- or C4-C18cycloalkenyl which is substituted by E and/or interrupted by D;
- L is E;
- K;
- C6-C18aryl;
- or C6-C18aryl which is substituted by G, E and/or K;
- R4 is C6-C18aryl;
- C6-C18aryl which is substituted by C1-C18alkyl, C1-C18alkoxy;
- C1-C18alkyl;
- or C1-C18alkyl which is interrupted by —O—;
- R7 is H;
- C6-C18aryl;
- C6-C18aryl which is substituted by C1-C18alkyl C1-C18alkoxy;
- C1-C18alkyl;
- C1-C18alkyl which is interrupted by —O—;
- R8 is H;
- C6-C18aryl:
- C6-C18aryl which is substituted by C1-C18alkyl, C1-C18alkoxy;
- C1-C18alkyl;
- C1-C18alkyl which is interrupted by —O—;
- or two substituents selected from V1 to V5, W1 to W5, X1 to X5, Y1 to Y5 which are in neighborhood to each other form a five to seven membered ring.
113 more elements
An electroluminescent device according to claim 17, wherein the pyrimidine compound has the following formula
- wherein
- V is H, or C1-C8-alkyl,
- X3 and X4 are independently of each other H, C1-C8alkyl, C1-C8alkoxy, C1-C8thioalkyl, or phenyl,
- X5 is H, or C1-C8alkoxy,
- W5 is H, C1-C8alkyl, or O(CH2)n1—X,
- Y5 is H, C1-C8alkyl, or O(CH2)n1—X,
- Y3, Y4, W3 and W4 are independently of each other C1-C8alkyl, C1-C8alkoxy, C1-C8thioalkyl, halogen, in particular Br, phenyl, or O(CH2)n1—X, wherein n1 is an integer of 1 to 5 and X is —O—(CH2)m1CH3, —OC(O)—(CH2)m1CH3, —C(O)—O—C1-C8alkyl, —NR103R104, wherein m1 is an integer of 0 to 5 and R103 and R104 are independently of each other H, or C1-C8-alkyl, or R103 and R104 together form a five or six membered heterocyclic ring;
- or the following formula
- wherein
- V is H, or C1-C8alkyl,
- W3 is H, C1-C8alkyl, or C1-C8alkoxy,
- X3 is H, C1-C8alkoxy, phenyl or O(CH2)n1—X,
- X5 is H, C1-C8alkoxy, phenyl or O(CH2)n1—X,
- Y3 is H, C1-C8alkyl, or C1-C8alkoxy, wherein n1 is an integer of 1 to 4 and X is —O—(CH2)m1CH3, —OC(O)—(CH2)m1CH3, —C(O)—O—C1-C8alkyl, wherein m1 is an integer of 0 to 5;
- or the following formula
- wherein
- W3 and W4 are independently of each other H, —NR103R104, C1-C8thioalkyl, or C1-C8alkoxy,
- Y3 and Y4 are independently of each other H, —NR103R104, C1-C8thioalkyl, or C1-C8alkoxy, wherein
- R103 and R104 are independently of each other H, or C1-C8alkyl.
- W5 is H, C1-C8alkyl, or O(CH2)n1—X,
- Y5 is H, C1-C8alkyl, or O(CH2)n1—X,
- wherein n1 is an integer of 1 to 5 and X is —O—(CH2)m1CH3, —OC(O)—(CH2)m1CH3, —C(O)—O—C1-C8alkyl, —NR103R104, wherein m1 is an integer of 0 to 5 and R103 and R104 are independently of each other H, or C1-C8-alkyl, or R103 and R104 together form a five or six membered heterocyclic
- or the following formula
- wherein
- W3 is H, —NR103R104, C1-C8thioalkyl, or C1-C8alkoxy,
- Y3 is H, —NR103R104, C1-C8thioalkyl, or C1-C8alkoxy, wherein R103 and R104 are independently of each other H, or C1-C8alkyl,
- R101 and R102 are independently of each other H, C1-C8alkyl, phenyl, or C5-C7cycloalkyl, in particular cyclohexyl;
- or the following formula
- wherein
- Y3 is H, —NR103R104, C1-C8thioalkyl, or C1-C8alkoxy,
- X3 is H, —NR103R104, C1-C8thioalkyl, or C1-C8alkoxy, wherein R103 and R104 are independently of each other H, or C1-C8alkyl;
- or the following formula
- wherein
- Y3 is H, —NR103R104, C1-C8thioalkyl, or C1-C8alkoxy,
- X3 is H, —NR103R104, C1-C8thioalkyl, or C1-C8alkoxy, wherein R103 and R104 are independently of each other H, or C1-C8alkyl, and R101 and R102 are independently of each other H, C1-C8alkyl, phenyl, or C5-C7cycloalkyl.
32 more elements
An electroluminescent device according to claim 17, wherein W and Y are groups of the formula
An electroluminescent device according to claim 18, comprising a pyrimidine compound of formula
An electroluminescent device according to claim 17, comprising a pyrimidine compound of formula I, wherein V is hydrogen, W and Y are independently of each other a group of formula
- X is a group of formula
- wherein
- R11, R12, R13, R14, R15, R16 and R17 are independently of each other H, C6-C18aryl;
- C6-C18aryl which is substituted by E;
- E, C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C6-C18aryl;
- C6-C18aryl which is substituted by E;
- R18 and R19 are independently of each other H, C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C6-C18aryl;
- C6-C18aryl which is substituted by E;
- D is —CO—;
- —COO—;
- —OCOO—;
- —S—;
- —SO—;
- —SO2—;
- —O—;
- —NR5—;
- —SiR5R6—;
- —POR5—;
- —CR5═CR6—;
- or —C≡C—;
- E is —OR5;
- —SR5;
- —NR5R6;
- —COR8;
- —COOR7;
- —CONR5R6;
- —CN;
- —OCOOR7;
- or halogen
- R7 is H;
- C6-C18aryl;
- C6-C18aryl which is substituted by C1-C18alkyl. C1-C18alkoxy:
- C1-C18alkyl;
- C1-C18alkyl which is interrupted by —O—;
- R8 is H;
- C6-C18aryl;
- C6-C18aryl which is substituted by C1-C18alkyl, C1-C18alkoxy;
- C1-C18alkyl;
- C1-C18alkyl which is interrupted by —O—;
- or two substituents selected from V1 to V5, W1 to W5, X1 to X5, Y1 to Y5 which are in neighborhood to each other form a five to seven membered ring.
41 more elements
An electroluminescent device according to claim 17, comprising a pyrimidine compound of formula
- wherein W3 and Y3 are a group of formula
- wherein
- R110 is C6-C10-aryl, C6-C10-aryl which is substituted by C1-C6-alkyl, C1-C4-alkoxy
- or C4-C10 heteroaryl,
- X3 is H, C1-C6-alkyl, C1-C4-alkoxy, Ph, or
2 more elements
A pyrimidine compound according to claim 17 of formula
- wherein
- W is
A primidine compound according to claim 17 of formula
- wherein Ar is a group of formula
- W11 to W15, W21 to W25, W31 to W35, W41 to W45, Y11 to Y15, Y21 to Y21, Y31 to Y35 and Y41 to Y45 are independently of each other H;
- C6-C24aryl;
- C6-C24aryl which is substituted by G;
- C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C7-C18alkylaryl;
- C7-C18alkylaryl which is substituted by E and/or interrupted by D;
- C2-C18alkenyl;
- C2-C18alkenyl which is substituted by E and/or interrupted by D;
- C2-C18alkynyl;
- C2-C18alkynyl which is substituted by E and/or interrupted by D;
- C1-C18alkoxy, C1-C18alkoxy which is substituted by E and/or interrupted by D;
- —SR5;
- —NR5R6;
- C2-C24heteroaryl;
- C2-C24heteroaryl which is substituted by L;
- —SOR4;
- —SO2R4;
- —COR8;
- —COOR7;
- —CONR5R6;
- C4-C18cycloalkyl;
- C4-C18cycloalkyl which is substituted by E and/or interrupted by D;
- C4-C18cycloalkenyl;
- C4-C18cycloalkenyl which is substituted by E and/or interrupted by D;
- V is H;
- C6-C24aryl;
- C6-C24aryl which is substituted by G;
- C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C7-C18alkylaryl;
- C7-C18alkylaryl which is substituted by E and/or interrupted by D;
- C2-C18alkenyl;
- C2-C18alkenyl which is substituted by E and/or interrupted by D;
- C2-C18alkynyl;
- C2-C18alkynyl which is substituted by E and/or interrupted by D;
- C1-C18alkoxy, C1-C18alkoxy which is substituted by E and/or interrupted by D;
- —SR5;
- or —NR5R6;
- C2-C24heteroaryl;
- C2-C24heteroaryl which is substituted by L;
- —SOR4;
- —SO2R4;
- —COR8;
- —COOR7;
- —CONR5R6;
- C4-C18cycloalkyl;
- C4-C18cycloalkyl which is substituted by E and/or interrupted by D;
- C4-C18cycloalkenyl;
- C4-C18cycloalkenyl which is substituted by E and/or interrupted by D;
- A18 and A19 are independently of each other H, C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C6-C18aryl;
- C6-C18aryl which is substituted by E,
- B11 to B14 and B21 to B24 are independently of each other H;
- C6-C18aryl;
- C6-C18aryl which is substituted by G;
- C1-C18alkyl;
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C7-C18alkylaryl;
- C7-C18alkylaryl which is substituted by E and/or interrupted by D;
- C2-C18alkenyl;
- C2-C18alkenyl which is substituted by E and/or interrupted by D;
- C2-C18alkynyl;
- C2-C18alkynyl which is substituted by E and/or interrupted by D;
- C1-C18alkoxy, C1-C18alkoxy which is substituted by E and/or interrupted by D;
- —SR5;
- —NR5R6;
- C2-C18heteroaryl;
- C2-C18heteroaryl which is substituted by L;
- —SOR4;
- —SO2R4;
- —COR8;
- —COOR7;
- or —CONR5R6;
- C4-C18cycloalkyl;
- C4-C18cycloalkyl which is substituted by E and/or interrupted by D;
- C4-C18cycloalkenyl;
- C4-C18cycloalkenyl which is substituted by E and/or interrupted by D;
- G is E:
- K;
- heteroaryl;
- heteroaryl which is substituted by C6-C18aryl;
- C6-C18aryl which is substituted by E and/or K;
- K is C1-C18alkyl:
- C1-C18alkyl which is substituted by E and/or interrupted by D;
- C7-C18alkylaryl which is substituted by E and/or interrupted by D;
- C2-C8alkenyl:
- C2-C18alkenyl which is substituted by E and/or interrupted by D;
- C2-C18alkynyl:
- C2-C18alkynyl which is substituted by E and/or interrupted by D;
- C1-C18alkoxy, C1-C18alkoxy which is substituted by E and/or interrupted by D:
- C4-C18cycloalkyl:
- C4-C18cycloalkyl which is substituted by E and/or interrupted by D:
- C4-C18cycloalkenyl;
- or C4-C18cycloalkenyl which is substituted by E and/or interrupted by Du
- L is E;
- K;
- C6-C18aryl;
- or C6-C18aryl which is substituted by G, E and/or K;
- R4 is C6-C18aryl;
- C6-C18aryl which is substituted by C1-C18alkyl, C1-C18alkoxy;
- C1-C18alkyl;
- or C1-C18alkyl which is interrupted by —O—;
- R7 is H;
- C6-C18aryl;
- C6-C18aryl which is substituted by C1-C18alkyl, C1-C18alkoxy, C1-C18alkyl:
- C1-C18alkyl which is interrupted by —O—;
- R8 is H;
- C6-C18aryl;
- C6-C18aryl which is substituted by C1-C18alkyl, C1-C18alkoxy;
- C1-C18alkyl;
- C1-C18alkyl which is interrupted by —O—;
- or two substituents selected from V1 to V5, W1 to W5, X1 to X5, Y1 to Y5 which are in neighborhood to each other form a five to seven membered ring.
112 more elements
Dependencies are inferred from the claim text.