IP Library › Granted Patent US 9,079,872

Granted Patent B2

US 9,079,872 · App. 13/252,482 · Granted Jul 14, 2015

Phenanthro[9, 10-B]furans for electronic applications

Inventors: Thomas Schaefer (Liestal, CH); Christian Schildknecht (San Diego, CA); Peter Murer (Oberwil, CH); Christian Lennartz (Schifferstadt, DE); Nicolle Langer (Heppenheim, DE); Gerhard Wagenblast (Wachenheim, DE); Stefan Metz (Mannheim, DE)

Assignee: BASF SE

C07D307/77 C07D405/14

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Quick Facts

Patent No.: US 9,079,872
App. No.: 13/252,482
Granted: Jul 14, 2015
Kind: B2

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Abstract

The present invention relates to an electronic device, especially an electroluminescent devices, comprising a compound of the formula 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.

Claims (227)

1. A compound of formula (I):

wherein R 1 and R 2 are a group of formula

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;

wherein -L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula -NA 1 A 1′ , or a group

A 1 and A 1′ are independently of each other

A 1 and A 1′ together with a nitrogen atom to which they are bonded form a heteroaromatic ring, or form a structure

m′ is 0, 1, or 2; m1 can be 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 77 , —C(═O)OR 78 , or —C(═O)NR 75 R 76 ,

R 75 , R 76 and R 78 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—,

R 77 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; or C 1 -C 18 alkyl which is interrupted by —O—,

BU is

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 selected from the group consisting of cyclohexyl and cyclopentyl, 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 28 ,

R 28 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; or C 1 -C 18 alkyl which is interrupted by —O—,

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,

R 63 and R 64 are independently of each other 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—;

R 65 and R 66 are independently of each other 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—;

R 67 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; or C 1 -C 18 alkyl which is interrupted by —O—,

R 68 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; or C 1 -C 18 alkyl which is interrupted by —O—,

R 69 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; or C 1 -C 18 alkyl which is interrupted by —O—,

R 70 and R 71 are independently of each other C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, and

R 72 is C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl;

R 41 can be the same or different at each occurrence and is C1, 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, 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 and R 45′ are independently of each other a C 1 -C 25 alkyl group, a C 4 -C 18 cycloalkyl group, 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 ;

-L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula

wherein R 116′ is same as R 116 ;

-L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula

R 124 , R 125 and R 126 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 1 -C 18 fluoroalkyl, C 6 -C 24 aryl, which can optionally be substituted by G, C 2 -C 20 heteroaryl, which can optionally be 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.

2. The compound according to claim 1 , which is a compound of formula

wherein R 1 and R 2 are a group of formula

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;

wherein -L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula -NA 1 A 1′ , or a group

A 1 and A 1′ are independently of each other

A 1 and A 1′ together with a nitrogen atom to which they are bonded form a heteroaromatic ring, or form a structure

m′ is 0, 1, or 2; m1 can be same or different at each occurrence and is 0, 1, 2, 3, or 4;

R 77 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; or C 1 -C 18 alkyl which is interrupted by —O—,

BU is

R 119 and R 120 together form a group of formula ═CR 121 R 122 , wherein

R 28 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; or C 1 -C 18 alkyl which is interrupted by —O—,

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 , 13 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,

R 67 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; or C 1 -C 18 alkyl which is interrupted by —O—,

R 68 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; or C 1 -C 18 alkyl which is interrupted by —O—,

R 69 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; or C 1 -C 18 alkyl which is interrupted by —O—,

R 70 and R 71 are independently of each other C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, and

R 72 is C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl;

R 41 can be the same or different at each occurrence and is C1, 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, 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 and R 45′ are independently of each other a C 1 -C 25 alkyl group, a C 4 -C 18 cycloalkyl group, 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 ;

-L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula

wherein R 116′ is same as R 116 ;

-L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula

3. The compound according to claim 1 ,

wherein -L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula -NA 1 A 1′ , or a group

wherein

A 1 and A 1′ are independently of each other

or A 1 and A 1′ together with a 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 18 alkyl, which is optionally interrupted by —O—, or C 1 -C 18 alkoxy;

Bu is

wherein R 41 can be same or different at each occurrence and is C 1 -C 18 alkyl, which is optionally interrupted by —O—, or C 1 -C 18 alkoxy; m1 is 0, 1, or 2.

4. The compound according to claim 1 ,

wherein -L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula

5. The compound according to claim 1 ,

wherein -L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula

6. The compound according to claim 1 , which is selected from the group consisting of

Cpd.

R 1 = R 2

A 1

A 1′

A-1

A-2

A-3

A-4

A-5

A-8

Cpd.

R 1 = R 2

A 1

A 1′

B-1

B-2

B-3

B-4

B-5

B-8

Cpd.

R 1 = R 2

X 1

X 2

C-1

AR-1

C-2

AR-2

C-3

AR-3

Cpd.

R 1 = R 2

X 1

X 2

D-1

AR-1

D-2

AR-2

D-3

AR-3

Cpd.

R 1 = R 2

X 1

X 2

E-1

HE-1

E-2

HE-2

E-3

HE-3

E-4

HE-4

E-5

HE-5

E-6

HE-6

E-8

HE-8

E-9

HE-9

E-19

HE-10

Cpd.

R 1 = R 2

X 1

X 2

F-1

HE-1

F-2

HE-2

F-3

HE-3

F-4

HE-4

F-5

HE-5

F-6

HE-6

F-8

HE-8

F-9

HE-9

F-19

HE-10

7. A process for preparing the compound according to claim 1 , comprising:

reacting a compound of formula

with a compound of formula HNA 1 A 1′ ,

in the a presence of a base and a catalyst in a solvent,

wherein X 1 and X 2 are independently of each other -NA 1 A 1′ ,

m′ is 0, 1, or 2;

wherein X 11 and X 12 stand for halogen,

wherein

A 1 and A 1′ are independently of each other

A 1 and A 1′ together with the nitrogen atom to which they are bonded form a heteroaromatic ring, or form a structure

m1 can be same or different at each occurrence and is 0, 1, 2, 3, or 4;

R 77 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; or C 1 -C 18 alkyl which is interrupted by —O—,

wherein L 3 and L 4 are independently of each other a single bond, or a bridging unit BU,

BU is

R 119 and R 120 together form a group of formula ═CR 121 R 122 , wherein

R 28 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; or C 1 -C 18 alkyl which is interrupted by —O—,

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,

R 67 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; or C 1 -C 18 alkyl which is interrupted by —O—,

R 68 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; or C 1 -C 18 alkyl which is interrupted by —O—,

R 69 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; or C 1 -C 18 alkyl which is interrupted by —O—,

R 70 and R 71 are independently of each other C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, and

R 72 is C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl;

wherein R 1 and R 2 are a group of formula

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 205 , R 206 , R 207 , and R 208 are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is interrupted by O, C 1 -C 18 alkoxy, or C 1 -C 18 alkoxy which is interrupted by O, or C 1 -C 18 fluoroalkyl;

wherein R 41 can be the same or different at each occurrence and is C1, 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, 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 and R 45′ are independently of each other a C 1 -C 25 alkyl group, a C 4 -C 18 cycloalkyl group, 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 .

Assignments (3)

CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT APPL. NO. 14/901,736 PREVIOUSLY RECORDED AT REEL: 039460 FRAME: 0615. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 8, 2017

From: BASF SE

To: UDC IRELAND LIMITED

Reel/Frame 042740/0222 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2016

From: BASF SE

To: UDC IRELAND LIMITED

Reel/Frame 039460/0615 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 27, 2011

From: SCHAEFER, THOMAS; SCHILDKNECHT, CHRISTIAN; MURER, PETER; LENNARTZ, CHRISTIAN; LANGER, NICOLLE; WAGENBLAST, GERHARD; METZ, STEFAN

To: BASF SE

Reel/Frame 027447/0306 →

Continuity (2)

Provisional Application 61390622 · Oct 7, 2010

Related Publication 20120095222A1 · Apr 19, 2012