Organic electroluminescent materials and devices

• US 10,749,114 B2
• Filed: 07/27/2018
• Issued: 08/18/2020
• Est. Priority Date: 08/20/2013
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Adamovich, Vadim, Yamamoto, Hitoshi, Wang, Ting-Chih, Weaver, Michael S., Xia, Chuanjun, Alleyne, Bert, Boudreault, Pierre-Luc T., Dyatkin, Alexey Borisovich, Joseph, Scott
• Primary Examiner(s): Kosack, Joseph R
• Application Number:
  US16/047,123
• Publication Number:
  US 20180342680A1
• Time in Patent Office: 753 Days
• CPC Class Codes: C07D 213/06 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
• CPC Class Codes: C07D 213/22 containing two or more pyridine rings directly linked together, e.g. bipyridyl
• CPC Class Codes: C07D 213/26 Radicals substituted by halogen atoms or nitro radicals
• CPC Class Codes: C07D 215/06 having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 403/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 403/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 403/14 containing three or more hetero rings
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C07D 491/048 the oxygen-containing ring being five-membered
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 71/00 Manufacture or treatment specially adapted for the organic devices covered by this subclass
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/657 : Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: Y02E 10/549 : Organic PV cells

Abstract

A composition formed of a mixture of two compounds having similar thermal evaporation properties that are pre-mixed into an evaporation source that can be used to co-evaporate the two compounds into an emission layer in OLEDs via vacuum thermal evaporation process is disclosed.

Claims

1. A premixed co-evaporation source composition comprising:

a mixture of a first compound and a second compound for co-evaporation from one sublimation crucible;

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

wherein the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature;

wherein the first compound has an evaporation temperature T1 of 150 to 350°

C.;

wherein the second compound has an evaporation temperature T2 of 150 to 350°

C.;

wherein absolute value of T1−

T2 is less than 20°

C.;

wherein the first compound has a concentration C1 in said mixture and a concentration C2 in a film formed by evaporating the mixture in a vacuum deposition tool at a constant pressure between 1×

10<sup>−

6</sup> Torr to 1×

10<sup>−

9</sup> Torr, at a 2 Å

/sec deposition rate on a surface position at a predefined distance away from the mixture being evaporated;

wherein absolute value of (C1−

C2)/C1 is less than 5%;

wherein the first compound and the second compound each independently has the formula of Ir(L¹)₂(L²);

wherein L¹ has the formula;

2. The premixed co-evaporation source composition of claim 1, wherein the R_cc of the first compound is benzene, which may be substituted, and the Rcc of the second compound is pyridine, which may be substituted.

3. The premixed co-evaporation source composition of claim 1, wherein each L¹ is selected from the group consisting of:

4. An organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer comprising the premixed co-evaporation source composition according to claim 1.

5. The premixed co-evaporation source composition of claim 1, wherein L² of the first compound is selected from the group consisting of:

6. The premixed co-evaporation source composition of claim 1, wherein the first compound is selected from the group consisting of:

7. The premixed co-evaporation source composition of claim 6, wherein the mixture of the first compound and the second compound is selected from the group consisting of:

(Compound 7 and Compound

     130), (Compound 8 and Compound

     131), (Compound 25 and Compound

     131), (Compound 27 and Compound

     135), (Compound 20 and Compound

     145), (Compound 25 and Compound

     148), (Compound 40 and Compound

     174), (Compound 103 and Compound

     204), and (Compound 116 and Compound

     217).