IP Library Granted Patent US 7,282,275
Granted Patent B2
US 7,282,275 · App. 10/414,066 · Granted Oct 16, 2007

Materials for organic electronic devices

Assignee: 3M Innovative Properties Company
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Quick Facts
Patent No.
US 7,282,275
App. No.
10/414,066
Granted
Oct 16, 2007
Kind
B2
Abstract

The invention provides compositions, organic electronic devices, and methods for preparing organic electronic devices. The compositions include a small molecule that is combined with at least one other material selected from a charge transporting material, a charge blocking material, a light emitting material, a color conversion material, or a combination thereof. The first compound has an aromatic core and two to four identical end capping groups attached to the aromatic core. The second compound has at least some structural similarities to the first compound of the composition.

Claims (121)

1. A composition comprising:

(a) a first compound of Formula I

that is a charge transporting material, a charge blocking material, a light emitting material, a color conversion material, or a combination thereof,

wherein

Ar 1 is a first aromatic core and is a divalent, trivalent, or tetravalent radical of

that is unsubstituted or substituted with one or more substituents selected from alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, diarylamino, cyano, nitro, ester, heteroalkyl, heteroaryl, and combinations thereof;

EC is a first end capping group and is a monovalent radical of

that is unsubstituted or substituted with one or more substituents selected from alky), alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, diarylamino, cyano, nitro, ester, heteroalkyl, heteroaryl, and combinations thereof;

n is an integer of 2 to 4, wherein the first end capping groups are identical; and

each R is independently an alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, diarylamino, cyano, nitro, ester, heteroalkyl, heteroaryl, or combinations thereof;

each R 1 is independently a hydrogen, alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, diarylamino, cyano, nitro, ester, heteroalkyl, heteroaryl, or combinations thereof;

X is O, S, or NR 2 where R 2 is a C 1-30 alkyl, a C 1-30 heteroalkyl, a C 6-20 aryl, a C 3-20 heteroaryl, or a combination thereof;

A is C, Si, Ge, Pb, or Sn;

Z is NH or CH 2 ;

t is an integer of 0 to4; and

(b) a second compound that is selected from a charge transporting material, a charge blocking material, a light emitting material, a color conversion material, or a combination thereof, said second compound being a polymeric material having

an aromatic radical that comprises the first aromatic core of the first compound, wherein the aromatic radical of the second compound can be unsubstituted, substituted with a substituent of a same type that is present on the first aromatic core of the first compound, or substituted with a substituent that is absent on the first aromatic core of the first compound,

a second end capping group that comprises the first end capping group of the first compound, wherein the second end capping group can be unsubstituted, substituted with a substituent of a same type that is present on the first end capping group, or substituted with a substituent that is absent on the first end capping group;

a divalent radical that comprises a divalent radical of the first end capping group of the first compound, wherein the divalent radical in the second compound can be unsubstituted, substituted with a substituent of a same type that is present on the first end capping group, or substituted with a substituent that is absent on the first end capping group; or

a combination thereof,

wherein the composition is amorphous and solution processible.

2. The composition of claim 1 , wherein the second compound is a light emitting polymer.

3. The composition of claim 1 , wherein the second compound is an electroactive polymer.

4. The composition of claim 1 , wherein the second compound is a polymer comprising the reaction product of a monomer mixture comprising a first monomer comprising the fist aromatic core of the first compound.

5. The composition of claim 1 , wherein the second compound is a polymer that is the reaction product of a monomer mixture comprising a first monomer comprising the first end capping group or a radical of the first end capping group.

6. The composition of claim 1 , wherein the second compound has an aromatic moiety that comprises the first aromatic core of the first compound, said first aromatic core being a divalent, trivalent, or tetravalent radical of

that is unsubstituted or substituted with one or more substituents selected from C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, fluoro, C 1-20 fluoroalkyl, C 1-20 perfluoroalkyl, C 12-20 diarylamino, cyano, nitro, C 2-20 ester, C 1-20 heteroalkyl, C 3-20 heteroaryl, and combinations thereof,

wherein

Z is NH or CH 2 ; and

A is C, Si, Ge, Pb, or Sn;

each R is independently an C 1-30 alkyl, C 2-30 alkenyl, C 1-30 alkoxy, C 6-30 aryl, C 6-30 aryloxy, fluoro, C 1-30 fluoroalkyl, C 1-30 perfluoroalkyl, C 12-30 diarylamino, cyano, nitro, C 2-30 ester, C 1-30 heteroalkyl, C 3-30 heteroaryl, or combinations thereof; and

each R 1 independently a hydrogen, C 1-30 alkyl, C 2-30 alkenyl, C 1-30 alkoxy, C 6-30 aryl, C 6-30 aryloxy, fluoro, C 1-30 , fluoroalkyl, C 1-30 perfluoroalkyl, C 12-30 diarylamino, cyano, nitro, C 2-30 ester, C 1-30 heteroalkyl, C 3-30 heteroaryl, or combinations thereof.

7. The composition of claim 1 , wherein the second compound has an aromatic moiety that comprises the first aromatic core of the first compound, said first aromatic core being a divalent, trivalent, or tetravalent radical of

that is unsubstituted or substituted with one or more substituents selected from C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, fluoro, C 1-20 fluoroalkyl, C 1-20 perfluoroalkyl, C 12-20 diarylamino, cyano, nitro, C 2-20 ester, C 1-20 heteroalkyl, C 3-20 heteroaryl, and combinations thereof,

wherein

each R is independently an C 1-30 alkyl, C 2-30 alkenyl, C 1-30 alkoxy, C 6-30 aryl, C 6-30 aryloxy, fluoro, C 1-30 fluoroalkyl, C 1-30 perfluoroalkyl, C 12-30 diarylamino, cyano, nitro, C 2-30 ester, C 1-30 heteroalkyl, C 3-30 heteroaryl, or combinations thereof;

X is O, S, or NR 2 where R 2 is a C 1-30 alkyl, a C 1-30 heteroalkyl, a C 6-20 aryl, a C 3-20 heteroaryl, or a combination thereof; and

t is an integer from 1 to an integer of 0 to 4.

8. The composition of claim 1 , wherein the second compound has an aromatic moiety that comprises the first aromatic core of the first compound, said first aromatic core being a divalent, trivalent, or tetravalent radical of

that is unsubstituted or substituted with one or more substituents selected from C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, fluoro, C, 1-20 fluoroalkyl, C 1-20 perfluoroalkyl, diarylamino, cyano, nitro, ester, C 1-20 heteroalkyl, C 3-20 heteroaryl, and combinations thereof,

wherein

X is O, S, or NR 2 where R 2 is a C 1-30 alkyl, a C 1-30 heteroalkyl, a C 6-20 aryl, a C 3-20 heteroaryl, or a combination thereof.

9. The compositions of claim 1 , wherein the second compound has an aromatic moiety tat comprises the first aromatic core of the first compound, said first aromatic core being selected from

wherein

each R 3 is independently hydrogen, C 1-30 alkyl, C 6-20 aryl, C 3-20 heteroaryl, or C 1-30 heteroalkyl containing one or more atoms of S, N, O, P, or Si; and

each R 4 is independently C 1-30 alkyl, C 6-20 aryl, C 3-20 heteroaryl, or C 1-30 heteroalkyl containing one or more atoms of S, N, O, P, or Si.

10. The composition of claim 1 , wherein the second compound has a second end capping group that comprises the first end capping group or the second compound comprises a divalent radical of the first end capping group, said first end capping group selected from

wherein

each Ph is phenyl;

each R 3 is independently hydrogen, C 1-30 alkyl, C 6-20 aryl, C 3-20 heteroaryl, C 1-30 heteroalkyl, or combinations thereof; and each R 4 is independently C 1-30 alkyl, C 6-20 aryl, C 3-20 heteroaryl, C 1-30 heteroalkyl; or combinations thereof.

11. The composition of claim 10 , wherein R 3 or R 4 is methyl or phenyl.

12. The composition of claim 1 , wherein the second compound has a second end capping group that comprises the first end capping group or the second compound comprises a divalent radical of the first end capping group, said first end capping group being a C 6-60 carbocyclic aryl that is a monovalent radical of

that is unsubstituted or substituted with one or more groups selected from C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, fluoro, C 1-20 fluoroalkyl, C 1-20 perfluoroalkyl, C, 12-20 diarylamino, cyano, nitro, C 2-20 ester, C 1-20 heteroalkyl, C 3-20 heteroaryl, and combinations thereof,

wherein each R is independently an C 1-30 alkyl, C 2-30 alkenyl, C 1-30 alkoxy, C 6-30 aryl, C 6-30 aryloxy, fluoro, C 1-30 fluoroalkyl, C 1-30 perfluoroalkyl, C 12-30 diarylamino, cyano, nitro, C 2-30 ester, C 1-30 heteroalkyl, C 3-30 heteroaryl, or combinations thereof.

13. The composition of claim 1 , wherein the second compound has a second end capping group that comprises the first end capping group or the second compound comprises a divalent radical of the first end capping group, said first end capping group being a C 3-60 heteroaryl having an imine linkage and a monovalent radical of

that is unsubstituted or substituted with one or more groups selected from C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, fluoro, C 1-20 fluoroalkyl, C 1-20 perfluoroalkyl, diarylamino, cyano, nitro, ester, C 1-20 heteroalkyl, C 3-20 heteroaryl, and combinations thereof,

wherein

each R is independently an C 1-30 alkyl, C 2-30 alkenyl, C 1-30 alkoxy, C 6-30 aryl, C 6-30 aryloxy, fluoro, C 1-30 fluoroalkyl, C 1-30 perfluoroalkyl, C 12-30 diarylamino, cyano, nitro, C 2-30 ester, C 1-30 heteroalkyl, C 3-30 heteroaryl, or combinations thereof; and

X is O, S, or NR 2 where R 2 is a C 1-30 alkyl, a C 1-30 heteroalkyl, a C 6-20 aryl, a C 3-20 heteroaryl, or a combination thereof.

14. The composition of claim 1 , wherein the second compound has a second end capping group that comprises the first end capping group or the second compound comprises a divalent radical of the first end capping group, said first end capping group being a C 6-60 aromatic amino aryl or a C 3-60 heteroaryl that is electron rich and a monovalent radical of

that is unsubstituted or substituted with one or more groups selected from C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, fluoro, C, 1-20 fluoroalkyl, C 1-20 perfluoroalkyl, C 12-20 diarylamino, cyano, nitro, C 2-20 ester, C 1-20 heteroalkyl, C 3-20 heteroaryl, and combinations thereof,

wherein

each R is independently an C 1-30 alkyl, C 2-30 alkenyl, C 1-30 alkoxy, C 6-30 aryl, C 6-30 aryloxy, fluoro, C 1-30 fluoroalkyl, C 1-30 perfluoroalkyl, C 12-30 diarylamino, cyano, nitro, C 2-30 ester, C 1-30 heteroalkyl, C 3-20 heteroaryl, or combinations thereof; and

each X is independently O, S, or NR 2 where R 2 is a C 1-30 alkyl, a C 1-30 heteroalkyl, a C 6-20 aryl, a C 3-20 heteroaryl, or a combination thereof.

15. The composition of claim 1 , wherein the composition comprises a hole transporting material and an electron transporting material.

16. The composition of claim 1 , wherein the composition comprises a hole transporting material, an electron transporting material, and a light emitting material.

17. The composition of claim 1 , wherein R, R 1 or a substituent on the first compound comprises at least one soft segment comprising a divalent poly(oxyalkylene) segment of formula

or a divalent poly(dialkylsiloxane) segment of formula

where m is an integer of 1 to 6, y is an integer of 2 to 20, and w is an integer of 1 to 10.

18. The composition of claim 1 , wherein R, R 1 , or a substituent on the first compound comprises at least one fluoro, fluoroalkyl, or perfluoroalkyl group.

19. The composition of claim 1 , wherein n is equal to 2.

20. A composition comprising:

(a) a first compound of Formula II

that is a light emitting material, a charge transporting material, a charge blocking material, or a combination thereof,

wherein

Ar 1 is a first aromatic core and is a divalent radical selected from

EC are two identical first end capping groups selected from

wherein

each Ph is phenyl; and

each R 3 is independently hydrogen, C 1-30 alkyl, C 6-20 aryl, C 3-20 heteroaryl, or C 1-30 heteroalkyl;

each R 4 is independently C 1-30 alkyl, C 6-20 aryl, C 3-20 heteroaryl, or C 1-30 heteroalkyl; and

(b) a second compound that is selected from a charge transporting material, a charge blocking material, a light emitting material, a color conversion material, or a combination thereof, said second compound being a polymeric material having

an aromatic radical that comprises the first aromatic core of the first compound, wherein the aromatic radical of the second compound can be unsubstituted, substituted with a substituent of a same type that is present on the first aromatic core of the first compound, or substituted with a substituent that is absent on the first aromatic core of the first compound;

a second end capping group that comprises the first end capping group of the first compound, wherein the second end capping group can be unsubstituted, substituted with a substituent of a same type that is present on the first end capping group, or substituted with a substituent that is absent on the first end capping group;

a divalent radical that comprises a divalent radical of the first end capping group of the first compound, wherein the divalent radical in the second compound can be unsubstituted, substituted with a substituent of a same type that is present on the first end capping group, or substituted with a substituent that is absent on the first end capping group;

or a combination thereof,

wherein the composition is amorphous and solution processible.

21. A composition comprising:

(b) a first compound of Formula I

that is a charge transporting material, a charge blocking material, a light emitting material, a color conversion material, or a combination thereof,

wherein

Ar 1 is a first aromatic core and is a divalent, trivalent, or tetravalent radical of

that is unsubstituted substituted with one or more substituents selected from alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, diarylamino, cyano, nitro, ester, heteroalkyl, heteroaryl, and combinations thereof;

EC is a first end capping group that is a C 6-60 carbocyclic aryl, a C 3-60 heteroaryl, a C 12-30 aromatic amino aryl, or a monovalent radical of a silsesquioxane that is unsubstituted or substituted with one or more substituents selected from alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, diarylamino, cyano, nitro, ester, heteroalkyl, heteroaryl, and combinations thereof;

n is an integer of 2 to 4, wherein the first end capping groups are identical;

each R is independently an alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, diarylamino, cyano, nitro, ester, heteroalkyl, heteroaryl, or combinations thereof;

each R 1 independently a hydrogen, alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, diarylamino, cyano, nitro, ester, heteroalkyl, heteroaryl, or combinations thereof;

X is O, S, or NR 2 where R 2 is a C 1-30 alkyl, a C 1-30 heteroalkyl, a C 6-20 aryl, a C 3-20 heteroaryl, or a combination thereof;

A is C, Si, Ge, Pb, or Sn;

Z is N or CH;

t is an integer of 0 to 4; and

(b) a second compound that is selected from a charge transporting material, a charge blocking material, a light emitting material, a color conversion material, or a combination thereof, said second compound being a polymeric material having

an aromatic radical that comprises the first aromatic core of the first compound, wherein the aromatic radical of the second compound can be unsubstituted, substituted with a substituent of a same type that is present on the first aromatic core of the first compound, or substituted with a substituent that is absent on the first aromatic core of the first compound;

a second end capping group that comprises the first end capping group of the first compound, wherein the second end capping group can be unsubstituted, substituted with a substituent of a same type that is present on the first end capping group, or substituted with a substituent that is absent on the first end capping group;

a divalent radical that comprises a divalent radical of the first end capping group of the first compound, wherein the divalent radical in the second compound can be unsubstituted, substituted with a substituent of a same type that is present on the first end capping group, or substituted with a substituent that is absent on the first end capping group;

or a combination thereof,

wherein the composition is amorphous and solution processible.

22. The composition of claim 21 , wherein the second compound has a second end capping group that comprises the first end capping group or the second compound comprises a divalent radical of the first end capping group, said first end capping group being a C 6-60 carbocyclic aryl comprising phenyl, biphenyl, anthryl, naphthyl, acenaphthyl, phenanthryl, dihydrophenathrenyl, anthracenyl, fluorenyl, 9-silafluorenyl, tetrahydropyrenyl, perylenyl, spirobisfluorenyl, fluoranthenyl, pyrenyl, dihydropyrenyl, tetrahydropyrenyl, rubrenyl, chrysenyl, or benzo[g,h,i]perylenyl,

wherein the first end capping group is unsubstituted or substituted with one or more groups selected from C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, fluoro, C 1-20 fluoroalkyl, C 1-20 perfluoroalkyl, C 2-20 diarylamino, cyano, nitro, C 2-20 ester, C 1-20 heteroalkyl, C 3-20 heteroaryl, and combinations thereof.

23. The composition of claim 21 , wherein the second compound has a second end capping group that comprises the first end capping group or the second compound comprises a divalent radical of the first end capping group, said first end capping group being a C 3-60 a heteroaryl comprising a furanyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, isothiazolyl, pyridinyl, pyridazinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothiophenyl, indolyl, carbazoyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, cinnolinyl, qiunazolinyl, quinoxalinyl, phthalazinyl, benzothiadiazolyl, benzotriazinyl, phenazinyl, phenanthridinyl, acridinyl, indazolyl, or siloles,

wherein the first end capping group is unsubstituted or substituted with one or more groups selected from C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, fluoro, C 1-20 fluoroalkyl, C 1-20 perfluoroalkyl, C 12-20 diarylamino, cyano, nitro, C 2-20 ester, C 1-20 heteroalkyl, C 3-20 heteroaryl, and combinations thereof.

24. The composition of claim 21 , wherein the second compound has a second end capping group that comprises the first end capping group or the second compound comprises a divalent radical of the first end capping group, said first end capping group being a C 12-60 tertiary aromatic amino aryl comprising a monovalent radical of diarylaniline, alkylcarbazole, arylcarbazole, tetraaryldiamine, starburst amine, peraryltriantine, dendridic amine, or spiroaxnine,

wherein the first end capping group is unsubstituted or substituted with one or more groups selected from C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, fluoro, C 1-20 fluoroalkyl, C 1-20 perfluoroalkyl, C 12-20 diarylamino, cyano, nitro, C 2-20 ester, C 1-20 heteroalkyl, C 3-20 heteroaryl, and combinations thereof.

25. The composition of claim 21 , wherein the second compound has a second end capping group that comprises the first end capping group or the second compound comprises a divalent radical of the first end capping group, said first end capping group being a C 12-60 tertiary aromatic amino aryl comprising a monovalent radical of N,N,N′N′-tetraarylbenzidine, N,N,N′,N′-tetraayl-1,4-phenylenediaxnine, N,N,N′N′- tetraryl-2,7-diaminofluorene, N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine, N,N′-bis(1-naphthyl)-N,N′-bis(phenyl)benzidine, 1,4-bis(carbazolyl)biphenyl, 4,4′4″-tris(N,N-diarylamino)triphenylamine, 1,3,5-tris(4-diarylaminophenyl)benzene, 4,4′,4″-tris(N,N-diphenylamino)triphenylamine, 4,4′,4″-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, or 1,3,5-tris(4-diphenylaminophenyl)benzene,

wherein the first end capping group is unsubstituted or substituted with one or more groups selected from C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, fluoro, C 1-20 fluoroalkyl, C 1-20 perfluoroalkyl, C 12-20 diarylamino, cyano, nitro, C 2-20 ester, C 1-20 heteroalkyl, C 3-20 heteroaryl, and combinations thereof.

26. The composition of claim 21 , wherein n is equal to 2.

27. An organic electronic device comprising the composition of claim 1 .

28. The organic electronic device of claim 27 , wherein organic electronic device is an organic electroluminescent device.

29. The organic electronic device of claim 28 , wherein the organic electroluminescent device comprises an organic emissive element comprising the first and second compound.

30. The organic electronic device of claim 29 , wherein the organic emissive element has multiple layers and the composition is in a light emitting layer.

31. The organic electronic device of claim 29 , wherein the organic emissive element has multiple layers and the composition is in a charge transporting layer, a charge blocking layer, a light emitting layer, a color conversion layer, or a combination thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2003
From: WOLK, MARTIN B.; BENTSEN, JAMES G.; ROBERTS, RALPH R.; STARAL, JOHN S.; LI, YINGBO
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 013971/0081 →
Continuity (2)
Provisional Application 6037385700 · Apr 19, 2002
Related Publication 20030219625A1 · Nov 27, 2003