Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9831437-B2
Application number	US-201414253471-A
Country	US
Kind code	B2
Filing date	Apr 15, 2014
Priority date	Aug 20, 2013
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

Abstract

A composition formed of a first mixture of a first compound and a second compound wherein the first compound has different chemical structure than the second compound; the first compound is capable of functioning as a hole transporting material in an organic light emitting device at room temperature; the first compound comprises at least one carbazole group; the first compound has a evaporation temperature T1 of 150 to 350° C.; the second compound has evaporation temperature T2 of 150 to 350° C.; the absolute value of T1−T2 is less than 20° C.; the first compound having a concentration C1 in said first mixture, and the first compound having a concentration C2 in a film formed by evaporating the first mixture in a vacuum deposition tool at a constant 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 the absolute value of (C1−C2)/C1 is less than 5%.

First claim

What is claimed is:

1. A composition comprising:
a mixture of a first host compound and a second host compound, wherein the first host compound has a different chemical structure than the second host compound;
wherein the first host compound is capable of functioning as a hole transporting material in an organic light emitting device at room temperature;
wherein the first host compound comprises at least one carbazole group;
wherein the first host compound has an evaporation temperature T1 of 150 to 350° C. and the second host compound has an evaporation temperature T2 of 150 to 350° C., wherein the evaporation temperature a compound is measured in a vacuum deposition tool at a constant 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 evaporating compound;
wherein the absolute value of T1−T2 is less than 20° C.;
wherein the first host compound has a concentration C1 in said mixture, and the first host compound has a concentration C2 in a film formed by evaporating the mixture in a vacuum deposition tool at a constant 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;
wherein the absolute value of (C1−C2)/C1 is less than 5%;
wherein the first host compound has a structure according to formula (I):

wherein
R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each represent mono, di, tri, tetra substitutions, or no substitution;
R 9 represents mono, di, tri substitutions, or no substitution;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 9 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
A 1 , A 2 , A 3 , A 4 , A 5 , and A 6 are each independently selected from N or C;
n is an integer from 1 to 20;

wherein the second host compound has a structure according to a formula (II):

wherein R 11 and R 12 each represent mono, di, tri, tetra substitutions, or no substitution;
Y is selected from the group consisting of O, S, Se, NR′, and CR″R′″;
L is a single bond or comprises an aryl or heteroaryl group having from 5-24 carbon atoms, which is optionally further substituted;
X 1 , X 2 , X 3 , X 4 , and X 5 are each independently selected from group consisting of CR and N;
at least one of X 1 , X 2 , X 3 , X 4 , and X 5 is N; and
R, R′, R″, and R′″ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

2. The composition of claim 1 , wherein the first host compound has evaporation temperature T1 of 200 to 350° C. and the second host compound has evaporation temperature of T2 of 200 to 350° C.

3. The composition of claim 1 , wherein the absolute value of (C1−C2)/C1 is less than 3%.

4. The composition of claim 1 , wherein the first host compound has a vapor pressure of P1 at T1, the second host compound has vapor pressure of P2 at T2; and
wherein the ratio of P1/P2 is within the range of 0.90 to 1.10.

5. The composition of claim 1 , wherein the first host compound has a first mass loss rate and the second host compound has a second mass loss rate, wherein the ratio between the first mass loss rate and the second mass loss rate is within the range of 0.90 to 1.10.

6. The composition of claim 1 , wherein the first host compound further comprises at least one of the chemical groups selected from the group consisting of triphenylene, dibenzothiophene, dibenzofuran, and dibenzoselenophene.

7. The composition of claim 1 , wherein the second host compound is capable of functioning as an electron transporting material in an organic light emitting device at room temperature.

8. The composition of claim 1 , wherein the composition further comprises a third host compound, wherein the third host compound has a different chemical structure than the first host and second host compounds, wherein the third host compound has an evaporation temperature T3 of 150 to 350° C., and wherein absolute value of T1−T3 is less than 20° C.

9. The composition of claim 1 , wherein the composition is in liquid form at a temperature lower than T1 and T2.

10. The composition of claim 1 , wherein the first host compound has a formula selected from the group consisting of:

11. The composition of claim 1 , wherein the first host compound has a formula selected from the group consisting of:

wherein R 7 and R 8 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

12. The composition of claim 1 , wherein the first host compound is selected from the group consisting of:

13. The composition of claim 1 , wherein X 1 , X 3 , and X 5 are N;
and wherein X 2 and X 4 are CR.

14. The composition of claim 1 , wherein the second host compound is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Zeng Lichang
• Adamovich Vadim
• Wang Ting-Chih
• Xia Chuanjun
• Weaver Michael S
• Yamamoto Hitoshi
• Alleyne Bert

Classifications

• H01L2251/5384

  Electricity · mapped topic

• H01L51/0054 Primary

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic