Organic electroluminescent element, compound for organic electroluminescent element, and light-emitting device, display device, and illumination device using said element

Patent metadata

Field	Value
Publication number	US-9825237-B2
Application number	US-201214238367-A
Country	US
Kind code	B2
Filing date	Aug 6, 2012
Priority date	Aug 18, 2011
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

An organic electroluminescent element using a compound represented by the following general formula (I) emits dark blue light and has small changes in the chromaticity and in the driving voltage even after driving for a long period of time:

wherein R 1 to R 6 ; Q 1 and Q 2 ; X 1 , X 2 , X 3 and X 4 are as defined herein.

First claim

The invention claimed is:

1. An organic electroluminescent element comprising:
a substrate;
a pair of electrodes including an anode and a cathode, disposed on the substrate; and
at least one organic layer including a light emitting layer, disposed between the electrodes,
wherein at least one kind of compound represented by the following general formula (I) is contained in the any layer of the at least one organic layer:

R 1 to R 6 each independently represent a hydrogen atom or a substituent, but there is no case where two adjacent groups out of R 1 to R 6 are bonded to each other to form a ring; Q 1 and Q 2 each independently represent a 6-membered aromatic ring or a 6-membered nitrogen-containing aromatic heterocycle; a ring may be further fused with the 6-membered ring represented by Q 1 and Q 2 ; of X 1 to X 4 , either each of X 1 and X 4 represents a single bond, and X 2 and X 3 each independently represents a linking group represented by any one of CR 51 R 52 , NR 53 , O, S, and SiR 54 R 55 , or each of X 2 and X 3 represents a single bond, and X 1 and X 4 each independently represents a linking group represented by any one of CR 51 R 52 , NR 53 , O, S, and SiR 54 R 55 ; R 51 to R 55 each independently represents a hydrogen atom or a substituent; wherein general formula (I) satisfies at least one of the following conditions 1 and 2:
condition 1 in which the number of carbon atoms constituting the 6-membered aromatic ring or the 6-membered nitrogen-containing aromatic heterocycle of Q 1 and the number of carbon atoms constituting the 6-membered aromatic ring or the 6-membered nitrogen-containing aromatic heterocycle of Q 2 are different from each other;
with the proviso that when one of Q 1 or Q 2 is a pyridine group and the other is a phenyl group, X 1 and X 4 are NR 53 , and each R 53 is a phenyl group, then at least one phenyl group of R 53 has at least one substituent; and

condition 2 in which the linking group represented by one of X 1 and X 2 and the linking group represented by one of X 3 and X 4 are different from each other.

2. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (I) is a compound represented by the following general formula (II-1):

wherein R 11 to R 16 each independently represents a hydrogen atom or a substituent, but there is no case where two adjacent groups out of R 11 to R 16 are bonded to each other to form a ring; Q 11 and Q 12 each independently represents a 6-membered aromatic ring or a 6-membered nitrogen-containing aromatic heterocycle; a ring may be further fused with the 6-membered ring represented by Q 11 and Q 12 ; X 11 and X 14 each independently represents a linking group represented by any one of CR 51 R 52 , NR 53 , O, S, and SiR 54 R 55 ; R 51 to R 55 each independently represents a hydrogen atom or a substituent; wherein general formula (II-1) satisfies at least one of the following conditions 1 and 2:
condition 1 in which the number of carbon atoms constituting the 6-membered aromatic ring or the 6-membered nitrogen-containing aromatic heterocycle of Q 11 and the number of carbon atoms constituting the 6-membered aromatic ring or the 6-membered nitrogen-containing aromatic heterocycle of Q 12 are different from each other;
with the proviso that when one of Q 11 or Q 12 is a pyridine group and the other is a phenyl group, X 11 and X 14 are NR 53 , and each R 53 is a phenyl group, then at least one phenyl group of R 53 has at least one substituent; and

condition 2 in which the linking group represented by X 11 and the linking group represented by X 14 are different from each other.

3. The organic electroluminescent element according to claim 2 , wherein the compound represented by the general formula (II-1) is a compound represented by the following general formula (II-2):

wherein R 61 to R 66 each independently represents a hydrogen atom or a substituent, but there is no case where two adjacent groups out of R 61 to R 66 are bonded to each other to form a ring; R 67 to R 74 each independently represents a hydrogen atom or a substituent, two adjacent groups out of R 67 to R 74 may be bonded to each other to form a ring structure, but the number of the rings thus formed is 2 or less; X 51 and X 54 each independently represents a linking group represented by any one of CR 51 R 52 , NR 53 , O, S, and SiR 54 R 55 ; R 51 to R 55 each independently represents a hydrogen atom or a substituent; wherein the linking group represented by X 51 and the linking group represented by X 54 are different from each other.

4. The organic electroluminescent element according to claim 3 , wherein in the general formula (II-2), X 51 and X 54 each independently represent a linking group represented by any one of CR 51 R 52 , NR 53 , and O.

5. The organic electroluminescent element according to claim 3 , wherein in the general formula (II-2), any one of X 51 and X 54 is a linking group represented by NR 53 , and the other is a linking group represented by any one of CR 51 R 52 and O.

6. The organic electroluminescent element according to claim 3 , wherein in the general formula (II-2), at least one of R 61 to R 74 and R 51 to R 55 is a substituent having any one of a fluorine atom, an alkyl group, a silyl group, an amino group, and a phenyl group or nitrogen-containing aromatic 6-membered ring having these groups.

7. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (I) is a compound represented by the following general formula (III-1):

R 21 to R 26 each independently represents a hydrogen atom or a substituent, but there is no case where two adjacent groups out of R 51 to R 25 are bonded to each other to form a ring; Q 21 and Q 22 each independently represent a 6-membered aromatic ring or a 6-membered nitrogen-containing aromatic heterocycle; a ring may be further fused with the 6-membered ring represented by Q 12 and Q 22 ; X 22 and X 23 each independently represent a linking group represented by any one of CR 51 R 52 , NR 53 , O, S, and SiR 54 R 55 ; R 51 to R 55 each independently represent a hydrogen atom or a substituent; wherein general formula (III-1) satisfies at least one of the following conditions 1 and 2;
condition 1 in which the number of carbon atoms constituting the 6-membered aromatic ring or the 6-membered nitrogen-containing aromatic heterocycle of Q 21 and the number of carbon atoms constituting the 6-membered aromatic ring or the 6-membered nitrogen-containing aromatic heterocycle of Q 22 are different from each other;
condition 2 in which the linking group represented by X 22 and the linking group represented by X 23 are different from each other.

8. The organic electroluminescent element according to claim 7 , wherein the compound represented by the general formula (III-1) is a compound represented by the following general formula (III-2):

R 81 to R 86 each independently represent a hydrogen atom or a substituent, but there is no case where two adjacent groups out of R 61 to R 66 are bonded to e

Assignees

• Takada Saki
• Takaku Koji
• Kitamura Tetsu
• Ise Toshihiro
• Sotoyama Wataru
• Udc Ireland Ltd

Inventors

• Takada Saki
• Takaku Koji
• Kitamura Tetsu
• Ise Toshihiro
• Sotoyama Wataru

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C07D235/18

  with aryl radicals directly attached in position 2 · CPC title

• H01L51/0054

  Electricity · mapped topic

• C07D221/18

  Ring systems of four or more rings · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title