Electroluminescent device with organic electroluminescent medium

• US 5,061,569 A
• Filed: 07/26/1990
• Issued: 10/29/1991
• Est. Priority Date: 07/26/1990
• Status: Expired due to Term

• Current Assignee: Global OLED Technology LLC (LG Display Co., Ltd.)
• Original Assignee: Eastman Kodak Company
• Inventors: O'Brien, Michael E., Tang, Ching W., VanSlyke, Steven A., Chen, Chin H.
• Primary Examiner(s): Seidleck, James J
• Application Number:
  US07/561,552
• Time in Patent Office: 460 Days
• Field of Search: 428/690, 428/917, 428/457, 428/515, 313/504, 313/506, 252/301.16
• US Class Current: 428/457
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/30 Coordination compounds
• CPC Class Codes: H10K 85/311 Phthalocyanine
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: Y10S 428/917 Electroluminescent
• CPC Class Codes: Y10T 428/31678 Of metal
• CPC Class Codes: Y10T 428/31909 Next to second addition polymer from unsaturated monomers

Abstract

An internal junction organic electroluminescent device is disclosed comprising in sequence, an anode, an organic hold injecting and transporting zone, an organic electron injecting and transporting zone, and a cathode. The hole injecting and transporting zone includes a tertiary amine containing at least two tertiary amine moieties and including attached to a tertiary amine nitrogen atom an aromatic moiety containing at least two fused aromatic rings.

Claims

1. An internal junction organic electroluminescent device comprising in sequence, an anode, an organic hole injecting and transporting zone comprised of a layer containing a hole transporting aromatic tertiary amine, an organic electron injecting and transporting zone, and a cathode, characterized in that

said hole transporting aromatic tertiary amine is comprised of at least two tertiary amine moieties and includes attached to a tertiary amine nitrogen atom an aromatic moiety containing at least two fused aromatic rings.

2. An internal junction organic electroluminescent device according to claim 1 further characterized in that said aromatic tertiary amine includes at least two aromatic groups attached to a tertiary amine nitrogen atom.

3. An internal junction organic electroluminescent device according to claim 2 further characterized in that said two aromatic groups each consist of an aromatic moiety containing at least two fused aromatic rings.

4. An internal junction organic electroluminescent device according to claim 2 further characterized in that said aromatic tertiary amine includes attached to a tertiary amine nitrogen atom three aromatic groups.

5. An internal junction organic electroluminescent device according to claim 4 further characterized in that said three aromatic groups each consist of an aromatic moiety containing at least two two fused aromatic rings.

6. An internal junction organic electroluminescent device according to claim 1 further characterized in that said aromatic tertiary amine includes at least two tertiary amine nitrogen atoms linked through a divalent aromatic moiety.

7. An internal junction organic electroluminescent device according to claim 6 further characterized in that said divalent aromatic moiety contains at least two fused aromatic rings.

8. An internal junction organic electroluminescent device according to claim 7 further characterized in that said tertiary amine nitrogen atoms are each linked to an aromatic moiety containing at least two fused aromatic rings.

9. An internal junction organic electroluminescent device according to claim 1 further characterized in that said aromatic moiety contains from 10 to 24 ring carbon atoms.

10. An internal junction organic electroluminescent device according to claim 9 further characterized in that said aromatic moiety contains from 10 to 16 carbon atoms.

11. An internal junction organic electroluminescent device according to claim 1 further characterized in that said aromatic moiety containing at least two fused aromatic rings is a naphthyl moiety.

12. An internal junction organic electroluminescent device according to claim 1 further characterized in that said aromatic tertiary amine satisfies the structural formula:

##STR10## wherein Q¹ and Q² are independently aromatic tertiary amine moieties and

G is a carbon to carbon bond or a linking group chosen from the class consisting of cycloalkylene having 5 to 7 ring carbon atoms, alkylene having from 1 to 6 carbon atoms, and a divalent arylene moiety consisting of at least one phenylene group or a naphthylene moiety.

13. An internal junction organic electroluminescent device according to claim 12 further characterized in that said aromatic tertiary amine is a triarylamine satisfying the structural formula:

##STR11## where R¹ and R² each independently represent a hydrogen atom, an aryl group, or an alkyl group of from 1 to 6 carbon atoms or R¹ and R² together represent the atoms completing a cycloalkyl group containing from 5 to 7 ring carbon atoms and

R³ and R⁴ each independently represent an aryl group which is in turn substituted with a diarylamino group, as indicated by the structural formula;

##STR12## wherein R⁵ and R⁶ are independently selected aryl groups, said aryl groups being independently chosen from the group consisting of phenyl, biphenyl and naphthyl moieties and at least one of said aryl groups being a naphthyl moiety.

14. An electroluminescent device according to claim 1 in which said aromatic tertiary amine is a tetraaryldiamine wherein the aryl groups are independently chosen from the group consisting of phenyl, biphenyl and naphthyl moieties and at least one of said aryl moieties is a naphthyl moiety.

15. An electroluminescent device according to claim 14 further characterized in that said tetraaryldiamine satisfies the formula:

##STR13## wherein Ar, Ar¹, Ar² and Ar³ are independently selected from among phenyl, biphenyl and naphthyl moieties,

L is a divalent naphthylene moiety or φ

_n,

φ

is a phenylene moiety,

n is an integer of from 1 to 4, and

at least one of Ar, Ar¹, Ar² and Ar³ is a naphthyl moiety when L is φ

_n.

16. An internal junction organic electroluminescent device according to claim 15 further characterized in that said tetraarylamine is chosen from the class consisting of

4,4'"'"'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl;

4,4"-bis[N-(1-naphthyl)-N-phenylamino]-p-terphenyl;

4,4'"'"'-bis[N-(2-naphthyl)-N-phenylamino]biphenyl;

4,4'"'"'-bis[N-(3-acenaphthenyl)-N-phenylamino]biphenyl;

1,5-bis[N-(1-naphthyl)-N-phenylamino]naphthalene;

4,4'"'"'-bis[N-(9-anthryl)-N-phenylamino]biphenyl;

4,4"-bis[N-(1-anthryl)-N-phenylamino]-p-terphenyl;

4,4'"'"'-bis[N-(2-phenanthryl)-N-phenylamino]biphenyl;

4,4'"'"'-bis[N-(8-fluoranthenyl)-N-phenylamino]biphenyl;

4,4'"'"'-bis[N-(2-pyrenyl)-N-phenylamino]biphenyl;

4,4'"'"'-bis[N-(2 naphthacenyl)-N-phenylamino]biphenyl;

4,4'"'"'-bis[N-(2 perylenyl)-N-phenylamino]biphenyl;

4,4'"'"'-bis[N-(1-coronenyl)-N-phenylamino]biphenyl;

2,6-bis(di-p-tolylamino)naphthalene;

2,6-bis[di-(1-naphtyl)amino]naphthalene;

2,6-bis[N-(1-naphthyl)-N-(2-naphthyl)amino]naphthalene;

N,N,N'"'"',N'"'"'-tetra(2 naphthyl) 4,4"-diamino-p-terphenyl;

18. An internal junction organic electroluminescent device according to claim 1 further characterized in that said hole injecting and transporting zone is comprised of

a hole injecting layer contacting said cathode and

a hole transporting layer containing said tertiary amine.

20. An internal junction organic electroluminescent device according to claim 18 in which said porphorinic compound is a metal containing porphorinic compound which satisfies the structural formula:

##STR14## wherein Q is --N═

or --C(R)═

;

M is a metal, metal oxide, or metal halide.,

R is hydrogen, alkyl, phenalkyl, phenyl, or alkylphenyl, each alkyl moiety containing from 1 to 6 carbon atoms, and

T¹ and T² represent hydrogen or together complete a unsaturated 6 membered ring containing ring atoms chosen from the group consisting of carbon, nitrogen, and sulfur atoms.

21. An internal junction organic electroluminescent device according to claim 18 in which said porphorinic compound is a metal free porphorinic compound which satisfies the structural formula:

##STR15## wherein Q is --N═

or --C(R)═

;

R is hydrogen, alkyl, phenalkyl, phenyl, or alkylphenyl, each alkyl moiety containing from 1 to 6 carbon atoms, and

T¹ and T² represent hydrogen or together complete a unsaturated 6 membered ring containing ring atoms chosen from the group consisting of carbon, nitrogen, and sulfur atoms.

22. An internal junction organic electroluminescent device according to claim 1 in which said electron injecting and transporting zone is comprised of a stilbene or chelated oxinoid compound.

23. An internal junction organic electroluminescent device according to claim 21 in which said chelated oxinoid compound is represented by the formula:

##STR16## wherein Me represents a metal;

n is an integer of from 1 to 3; and

Z independently in each occurrence represents the atoms completing a nucleus having at least two fused aromatic rings.

17. 4'"'"'-bis{N-phenyl-N-[4-(1-naphthyl)phenyl]-amino}biphenyl;

4,4'"'"'-bis[N-phenyl-N-(2-pyrenyl)amino]biphenyl;

2,6-bis[N,N-di(2-naphthyl)amine]fluorene; and

1,5-bis[N-(1-naphthyl)-N-phenylamino]naphthalene.

19. An internal junction organic electroluminescent device according to claim 17 further characterized in that said hole injecting layer contains a hole injecting porphorinic compound.