Organic light emitting device containing a hole injection enhancement layer

• US 5,998,803 A
• Filed: 05/29/1997
• Issued: 12/07/1999
• Est. Priority Date: 05/29/1997
• Status: Expired due to Term

• Current Assignee: Princeton University, University of Southern California
• Original Assignee: The Trustees of Princeton University (Princeton University), University of Southern California
• Inventors: Bulovic, Vladimir, Forrest, Stephen, Thompson, Mark E., Burrows, Paul
• Primary Examiner(s): Tran, Minh Loan
• Application Number:
  US08/865,491
• Time in Patent Office: 922 Days
• Field of Search: 257/40, 257/94, 257/96, 257/103, 313/503, 313/504, 313/506
• US Class Current: 257/40
• CPC Class Codes: B82Y 10/00 Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 2102/3026 Top emission
• CPC Class Codes: H10K 2102/321 Inverted OLED, i.e. having cathode between substrate and anode
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 50/81 Anodes
• CPC Class Codes: H10K 50/86 Arrangements for improving contrast, e.g. preventing reflection of ambient light
• CPC Class Codes: H10K 71/60 Forming conductive regions or layers, e.g. electrodes
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/621 Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide

Abstract

The present invention is directed to organic light emitting devices comprised of a heterostructure for producing electroluminescence, wherein the heterostructure includes a hole injection enhancement layer between a hole transporting layer and an indium tin oxide anode layer. The hole injection enhancement layer may be comprised of 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA), bis(1,2,5-thiadiazolo)-p-quinobis(1,3-dithiole) (BTQBT), or other suitable, rigid organic materials. The present invention is further directed to methods of fabricating such devices.

Claims

1. An organic light emitting device comprising:

a heterostructure for producing electroluminescence comprised of a hole injection enhancement layer between a hole transporting layer and an anode layer, wherein the hole injection enhancement layer is formed of a compound selected from a group consisting of 3,4,9,10-perylenetetracarboxylic dianhydride;

3,4,7,8-naphthalenetetracarboxylic dianhydride;

3,4,9,10-perylenetetracarboxylic dianhydride;

bis(1,2,5-thiadiazolo)-p-quinobis(1,3-dithiole);

1,4,5,8-naphthalenetetracarboxylic dianhydride;

##STR13## where R=H, alkyl or aryl;

##STR14## where R=H, alkyl or aryl;

a compound having the CA index name, bisbenzimidazo[2,1-a;

1'"'"',2'"'"'-b'"'"']anthra[2,1,9-def;

6,5,10-d'"'"'e'"'"'f'"'"']diisoquinoline-10,21-dione;

a compound having the CA index name, bisnaphth[2'"'"',3'"'"';

4,5]imidazo[2,1-a;

2'"'"',1'"'"'-a'"'"']anthra[2,1,9-def;

6,5,10-d'"'"'e'"'"'f'"'"']diisoquinoline-10,21-dione;

a compound having the CA index name, bisbenzimidazo[2,1-b;

2'"'"',1'"'"'-i]benzo[lmn][3,8]phenanthroline-8,1-dione;

a compound having the CA index name, benzo[lmn]bisnaphth[2'"'"',3'"'"';

4,5]imidazo[2,1-b;

2'"'"',1'"'"'-I][3,8]phenanthroline-9,20-dione;

or a substituted derivative of one of said compounds.

2. The organic light emitting device of claim 1 wherein the hole injection enhancement layer is comprised of 3,4,9,10-perylenetetracarboxylic dianhydride.

3. The organic light emitting device of claim 1 wherein said hole transporting layer is comprised of 4,4'"'"'-bis[N-(1-napthyl)-N-phenyl-amino]biphenyl.

4. The organic light emitting device of claim 1 wherein said electron transporting layer is comprised of aluminum-tris(8-hydroxyquinoline).

5. The organic light emitting device of claim 1 further comprising a cathode comprised of a Mg-Ag alloy.

6. The organic light emitting device of claim 1 further comprising a cathode comprised of a Li-Al alloy.

7. The organic light emitting device of claim 1 wherein said anode is comprised of indium tin oxide.

8. A display incorporating the organic light emitting device of claim 1.

9. A vehicle incorporating the organic light emitting device of claim 1.

10. A computer incorporating the organic light emitting device of claim 1.

11. A television incorporating the organic light emitting device of claim 1.

12. A printer incorporating the organic light emitting device of claim 1.

13. A wall, theater or stadium screen incorporating the organic light emitting device of claim 1.

14. A billboard or a sign incorporating the organic light emitting device of claim 1.

15. An organic light emitting device comprising:

a heterostructure for producing electroluminescence comprised of a hole injection enhancement layer between a hole transporting layer and an anode layer, wherein the hole injection enhancement layer is comprised of 3,4,9,10-perylenetetracarboxylic dianhydride.

16. A method of fabricating an organic light emitting device for producing electroluminescence comprising:

fabricating a heterostructure for producing electroluminescence, wherein the fabrication process includes the step of depositing a hole injection enhancement layer on a hole transporting layer and then depositing an indium tin oxide anode layer on said hole injection enhancement layer, wherein the hole injection enhancement layer is selected from the group consisting of 3,4,9,10-perylenetetracarboxylic dianhydride;

3,4,7,8-naphthalenetetracarboxylic dianhydride;

3,4,9,10-perylenetetracarboxylic dianhydride;

bis(1,2,5-thiadiazolo)-p-quinobis(1,3-dithiole);

1,4,5,8-naphthalenetetracarboxylic dianhydride;

##STR15## where R=H, alkyl or aryl;

##STR16## where R=H, alkyl or aryl;

a compound having the CA index name, bisbenzimidazo[2,1-a;

1'"'"',2'"'"'-b'"'"']anthra[2,1,9-def;

6,5,10-d'"'"'e'"'"'f'"'"']diisoquinoline-10,21-dione;

a compound having the CA index name, bisnaphth[2'"'"',3'"'"';

4,5]imidazo[2,1-a;

2'"'"',1'"'"'-a'"'"']anthra[2,1,9-def;

6,5,10-d'"'"'e'"'"'f'"'"']diisoquinoline-10,21-dione;

a compound having the CA index name, bisbenzimidazo[2,1-b;

2'"'"',1'"'"'-i]benzo[lmn][3,8]phenanthroline-8,1-dione;

a compound having the CA index name, benzo[lmn]bisnaphth[2'"'"',3'"'"';

4,5]imidazo[2,1-b;

2'"'"'1'"'"'-I][3,8]phenanthroline-9,20-dione;

or a substituted derivative of one of said compounds.

17. The method according to claim 16 wherein said hole injection enhancement layer is comprised of 3,4,9,10-perylenetetracarboxylic dianhydride.