IP Library › Granted Patent US 10,361,375
Granted Patent B2
US 10,361,375 · App. 14/863,887 · Granted Jul 23, 2019

Organic electroluminescent materials and devices

Inventors: Lichang Zeng (Lawrenceville, NJ); Chuanjun Xia (Lawrenceville, NJ); Scott Joseph (Ewing, NJ); Walter Yeager (Yardley, PA); Mingjuan Su (Ewing, NJ); Ting-Chih Wang (Lawrenceville, NJ)
Assignee: Universal Display Corporation
H01L51/0067C09K11/06H01L51/5016H01L51/5056H01L51/5096H01L2251/55H01L2251/556
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Quick Facts
Patent No.
US 10,361,375
App. No.
14/863,887
Granted
Jul 23, 2019
Kind
B2
Abstract

A composition formed of a mixture of a first compound and a second compound wherein the first compound has a different chemical structure than the second compound. The first compound and the second compound are both organic compounds. At least one of the first compound and the second compound contains at least one less abundant stable isotope atom. The first compound has an evaporation temperature T 1 and the second compound has an evaporation temperature T 2 where both T 1 and T 2 are between 100 to 400 ° C. and the absolute value of T 1 -T 2 is less than 20 ° C. The first compound has a concentration C 1 in said mixture and a concentration C 2 in a film formed by evaporating said mixture in a high vacuum deposition tool with a chamber base pressure between 1×10 −6 Torr to 1×10 −9 Torr, at a 2 Å/sec deposition rate on a surface positioned at a predefined distance away from the mixture being evaporated; and wherein absolute value of (C 1 -C 2 )/C 1 is less than 5%.

Claims (63)

1. A premixed co-evaporation source that is a mixture of a first compound and a second compound;

wherein the co-evaporation source is a co-evaporation source for vacuum deposition process;

wherein the first compound has a different chemical structure than the second compound;

wherein the first compound and the second compound are both organic compounds;

wherein the first compound comprises 3,3′-bicarbazole, and the second compound comprises triazine;

wherein the first compound and the second compound each independently further comprises dibenzothiophene or dibenzofuran;

wherein at least one of the first compound and the second compound contains at least one less abundant stable isotope atom;

wherein the first compound is a hole transporting compound, and the second compound is an electron transporting compound;

wherein the first compound has an evaporation temperature T 1 of 100 to 400° C.;

wherein the second compound has an evaporation temperature T 2 of 100 to 400° C.;

wherein absolute value of T 1 -T 2 is less than 20° C.;

wherein the first compound has a concentration C 1 in said mixture and a concentration C 2 in a film formed by evaporating the mixture in a high vacuum deposition tool with a chamber base pressure between 1×10 −6 Torr to 1×10 −9 Torr, at a 2 Å/sec deposition rate on a surface positioned at a predefined distance away from the mixture being evaporated; and

wherein absolute value of (C 1 -C 2 )/C 1 is less than 5%.

2. The premixed co-evaporation source of claim 1 , wherein the first compound has an evaporation temperature T 1 of 150 to 350° C. and the second compound has an evaporation temperature T 2 of 150 to 350° C.

3. The premixed co-evaporation source of claim 1 , wherein the first compound has an evaporation temperature T 1 of 200 to 350° C. and the second compound has an evaporation temperature T 2 of 200 to 350° C.

4. The premixed co-evaporation source of claim 1 , wherein absolute value of (C 1 -C 2 )/C 1 is less than 3%.

5. The premixed co-evaporation source of claim 1 , wherein the first compound has a vapor pressure of P 1 at T 1 at 1 atm, the second compound has a vapor pressure of P 2 at T 2 at 1 atm; and

wherein the ratio of P 1 /P 2 is within the range of 0.90 to 1.10.

6. The premixed co-evaporation source of claim 1 , wherein only one of the first compound and the second compound contains at least one stable, less abundant isotope atom.

7. The premixed co-evaporation source of claim 1 , wherein both of the first compound and the second compound each contains at least one stable less abundant isotope atom.

8. The premixed co-evaporation source of claim 1 , wherein the stable, less abundant isotope atom is deuterium or 13 C.

9. The premixed co-evaporation source of claim 1 , wherein the stable, less abundant isotope atom is deuterium; and wherein any carbon atom in the first compound or the second compound having deuterium atom is a non-conjugated carbon.

10. The premixed co-evaporation source of claim 1 , wherein at least one of the first compound and the second compound further comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophen.

11. The premixed co-evaporation source of claim 1 , wherein the first compound and the second compound each independently further comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophen.

12. A premixed co-evaporation source that is a mixture of a first compound and a second compound;

wherein the co-evaporation source is a co-evaporation source for vacuum deposition process;

wherein the first compound has a different chemical structure than the second compound;

wherein the first compound and the second compound are both organic compounds;

wherein the first compound comprises 3,3′-bicarbazole, and the second compound comprises triazine;

wherein the first compound and the second compound each independently further comprises dibenzothiophene or dibenzofuran;

wherein at least one of the first compound and the second compound contains at least one less abundant stable isotope atom;

wherein the first compound has an evaporation temperature T 1 of 100 to 400° C.;

wherein the second compound has an evaporation temperature T 2 of 100 to 400° C.;

wherein absolute value of T 1 -T 2 is less than 20° C.;

wherein the first compound has a concentration C 1 in said mixture and a concentration C 2 in a film formed by evaporating the mixture in a high vacuum deposition tool with a chamber base pressure between 1×10 −6 Torr to 1×10 −9 Torr, at a 2 Å/sec deposition rate on a surface positioned at a predefined distance away from the mixture being evaporated; and

wherein absolute value of (C 1 -C 2 )/C 1 is less than 5%, wherein one of the first compound and the second compound is a host compound, and the other of the first compound and the second compound is a fluorescent or delayed fluorescent emitter.

13. The premixed co-evaporation source of claim 1 , wherein the first compound and the second compound each has a purity in excess of 99% as determined by high pressure liquid chromatography.

14. The premixed co-evaporation source of claim 1 , wherein the composition further comprises a third compound, wherein the third compound has a different chemical structure than the first and second compounds, wherein the third compound has an evaporation temperature T 3 of 150 to 350° C., and wherein absolute value of T 1 -T 3 is less than 20° C.

15. A method for fabricating an organic light emitting device, the method comprising:

providing a substrate having a first electrode disposed thereon;

depositing a first organic layer over the first electrode by evaporating a pre-mixed co-evaporation source that is a mixture of a first compound and a second compound in a high vacuum deposition tool with a chamber base pressure between 1×10 −6 Torr to 1×10 −9 Torr, at a 2 Å/sec deposition rate on a surface position at a predefined distance away from the mixture being evaporated; and

depositing a second electrode over the first organic layer,

wherein the first compound has a different chemical structure than the second compound; wherein the first compound and the second compound are both organic compounds;

wherein the first compound comprises 3,3′-bicarbazole, and the second compound comprises triazine;

wherein the first compound and the second compound each independently further comprises dibenzothiophene or dibenzofuran;

wherein at least one of the first compound and the second compound contains at least one less abundant stable isotope atom;

wherein the first compound is a hole transporting compound, and the second compound is an electron transporting compound;

wherein the first compound has an evaporation temperature T 1 of 150 to 350° C.;

wherein the second compound has an evaporation temperature T 2 of 150 to 350° C.;

wherein absolute value of T 1 -T 2 is less than 20° C.;

wherein the first compound has a concentration Cl in said mixture and a concentration C 2 in the first organic layer; and

wherein absolute value of (C 1 -C 2 )/C 1 is less than 5%.

16. The premixed co-evaporation source of claim 12 , wherein the first compound has an evaporation temperature T 1 of 150 to 350° C. and the second compound has an evaporation temperature T 2 of 150 to 350° C.

17. The premixed co-evaporation source of claim 12 , wherein the first compound has an evaporation temperature T 1 of 200 to 350° C. and the second compound has an evaporation temperature T 2 of 200 to 350° C.

18. The premixed co-evaporation source of claim 12 , wherein absolute value of (C 1 -C 2 )/C 1 is less than 3%.

19. The premixed co-evaporation source of claim 12 , wherein the first compound has a vapor pressure of P 1 at T 1 at 1 atm, the second compound has a vapor pressure of P 2 at T 2 at 1 atm; and

wherein the ratio of P 1 /P 2 is within the range of 0.90 to 1.10.

20. The premixed co-evaporation source of claim 12 , wherein only one of the first compound and the second compound contains at least one stable, less abundant isotope atom.

21. The premixed co-evaporation source of claim 12 , wherein both of the first compound and the second compound each contains at least one stable less abundant isotope atom.

22. The premixed co-evaporation source of claim 12 , wherein the stable, less abundant isotope atom is deuterium or 13 C.

23. The premixed co-evaporation source of claim 12 , wherein the stable, less abundant isotope atom is deuterium; and wherein any carbon atom in the first compound or the second compound having deuterium atom is a non-conjugated carbon.

24. The premixed co-evaporation source of claim 12 , wherein at least one of the first compound and the second compound further comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophen.

25. The premixed co-evaporation source of claim 12 , wherein the first compound and the second compound each independently further comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophen.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 24, 2015
From: ZENG, LICHANG; XIA, CHUANJUN; JOSEPH, SCOTT; YEAGER, WALTER; SU, MINGJUAN; WANG, TING-CHIH
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 036648/0480 →
Continuity (3)
Provisional Application 62060192 · Oct 6, 2014
Provisional Application 62075333 · Nov 5, 2014
Related Publication 20160099422A1 · Apr 7, 2016
Cited By (9)
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