IP Library › Granted Patent US 10,636,973
Granted Patent B2
US 10,636,973 · App. 16/244,164 · Granted Apr 28, 2020

Polymer material, material for electroluminescence device, composition, thin film, and electroluminescence device comprising the same

Inventors: Fujiyama Takahiro (Yokohama, JP); Fumiaki Kato (Yokohama, JP); Takao Motoyama (Yokohama, JP); Yusaku Konishi (Yokohama, JP); Mitsunori Ito (Yokohama, JP); Furuta Keigo (Yokohama, JP)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
H01L51/0035C08G61/124C09K11/02H05B33/22C08G2261/12C08G2261/149C08G2261/1412C08G2261/1434C08G2261/312H01L51/502H01L51/5004H01L51/5056H01L2251/552
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Quick Facts
Patent No.
US 10,636,973
App. No.
16/244,164
Granted
Apr 28, 2020
Kind
B2
Abstract

A polymer material includes a structural unit represented by Chemical Formula 1 X—Y   Chemical Formula 1 wherein, in Chemical Formula 1, X and Y are as defined herein.

Claims (76)

1. A polymer material comprising a structural unit represented by Chemical Formula 1:

X—Y Chemical Formula 1

wherein, in Chemical Formula 1,

each X is the same or different, and is represented by Chemical Formula 2, and

each Y is the same or different, and is a substituted or unsubstituted C6 to C60 divalent aromatic cyclic group, a substituted or unsubstituted C6 to C60 divalent alicyclic cyclic group, a substituted or unsubstituted C3 to C60 divalent aromatic heterocyclic group, or a substituted or unsubstituted C3 to C60 divalent alicyclic heterocyclic group,

wherein, in Chemical Formula 2,

Ar 1 is a substituted or unsubstituted C6 to C60 trivalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 trivalent aromatic heterocyclic group,

Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C60 monovalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 monovalent aromatic heterocyclic group,

L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C60 divalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 divalent aromatic heterocyclic group,

each R 1 and R 2 are the same or different, and are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C60 monovalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 monovalent aromatic heterocyclic group,

or R 1 and R 2 are combined with each other to form one ring that is a pentagonal ring, a hexagonal ring, or a fused ring,

a is an integer ranging from 0 to 4,

b is an integer ranging from 0 to 3, and

Z 1 to Z 8 are each independently a nitrogen atom or —CH═.

2. The polymer material of claim 1 , wherein Y is a substituted or unsubstituted C6 to C60 divalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 divalent aromatic heterocyclic group.

3. The polymer material of claim 1 , wherein X is a group represented by one of Chemical Formulae 2-1 to 2-6:

wherein, in Chemical Formulae 2-1 to 2-6,

Ar 1 , Ar 2 , Ar 3 , L 1 , and L 2 are the same as in claim 1 ,

Ar 4 is a substituted or unsubstituted C6 to C60 monovalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 monovalent aromatic heterocyclic group, and

* is a linking point.

4. The polymer material of claim 3 , wherein L 1 and L 2 are each independently a single bond, a phenylene group, a biphenylene group, a fluorenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a naphthacenylene group, a pyrenylene group, a terphenylene group, a tolylene group, a t-butyl phenylene group, or a (phenylpropyl)phenylene group.

5. The polymer material of claim 1 , wherein Y is a group represented by one of Chemical Formulae 2-7 to 2-14:

wherein, in Chemical Formulae 2-7 to 2-14,

Ar 51 to Ar 55 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C6 to C60 monovalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 monovalent aromatic heterocyclic group,

A 11 to A 13 are each independently —O—, —S—, —Se—, —CR 3 R 4 —, or —SiR 5 R 6 — wherein R 3 to R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C3 to C60 heteroaryl group,

A 21 to A 28 are each independently —CR 7 ═, —N═, or —SiR 8 ═ wherein R 7 to R 8 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C3 to C60 heteroaryl group, and

* is a linking point.

6. The polymer material of claim 1 , wherein Ar 1 is a group represented by one of Chemical Formulae 2-15 to 2-26:

wherein, in Chemical Formulae 2-15 to 2-26,

A 61 is —O—, —S—, —Se—, —NR 61 — wherein R 61 is hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C3 to C60 heteroaryl group, or —CR 62 R 63 — wherein R 62 and R 63 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C3 to C60 heteroaryl group, and

* is a linking point.

7. The polymer material of claim 1 , wherein Ar 2 and Ar 3 are each independently a group represented by one of Chemical Formulae 2-27 to 2-70:

wherein, in Chemical Formulae 2-27 to 2-70,

R 71 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C60 monovalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 monovalent aromatic heterocyclic group,

wherein, in Chemical Formula 2-34, 2-35, 2-36, and 2-37, R K1 to R K8 are each independently a substituted or unsubstituted C1 to C20 alkyl group, and

* is a linking point.

8. The polymer material of claim 1 , wherein the polymer material comprises an alternating copolymer comprising the structural unit represented by Chemical Formula 1, and the alternating copolymer is represented by Chemical Formula 3:

E X—Y E m   Chemical Formula 3

wherein, in Chemical Formula 3,

each E is independently a substituted or unsubstituted C6 to C60 monovalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 monovalent aromatic heterocyclic group,

m is an integer of 2 or more, and

each X and each Y is independently the same or different.

9. The polymer material of claim 8 , wherein E is a group represented by one of Chemical Formulae 3-1 to 3-14:

wherein, in Chemical Formulae 3-1 to 3-14,

* is a linking point.

10. The polymer material of claim 1 , wherein a number average molecular weight (M n ) of the polymer material is about 10,000 grams per mole to about 1,000,000 grams per mole.

11. The polymer material of claim 1 , wherein a HOMO (highest occupied molecular orbital) energy level of the polymer material is about 5.5 electron Volts to about 6.0 electron Volts.

12. A material for an electroluminescence device, the material comprising the polymer material of claim 1 .

13. A composition comprising:

the polymer material of claim 1 ; and

at least one of a solvent or a dispersive medium.

14. A thin film comprising the polymer material of claim 1 .

15. An electroluminescence device comprising:

a pair of electrodes facing each other; and

at least one organic layer comprising the polymer material of claim 1 disposed between the pair of electrodes.

16. The electroluminescence device of claim 15 , wherein the at least one organic layer is formed by coating a composition comprising the polymer material.

17. The electroluminescence device of claim 15 , further comprising a quantum dot layer comprising a plurality of inorganic nanoparticles disposed between the pair of electrodes.

18. The electroluminescence device of claim 15 , wherein

the at least one organic layer comprises a hole transport layer, and

the hole transport layer comprises the polymer material.

19. A method for the manufacture of a polymer material, the method comprising:

providing at least one first monomer represented by Chemical Formula 4;

providing at least one second monomer represented by Chemical Formula 5; and

W 3 —Y—W 4   Chemical Formula 5

polymerizing the first monomer and the second monomer to obtain the polymer material,

wherein, in Chemical Formulae 4 and 5,

Ar 1 is a substituted or unsubstituted C6 to C60 trivalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 trivalent aromatic heterocyclic group,

Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C60 monovalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 monovalent aromatic heterocyclic group,

Y is a substituted or unsubstituted C6 to C60 divalent aromatic cyclic group, a substituted or unsubstituted C6 to C60 divalent alicyclic cyclic group, a substituted or unsubstituted C3 to C60 divalent aromatic heterocyclic group, or a substituted or unsubstituted C3 to C60 divalent alicyclic heterocyclic group,

L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C60 divalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 divalent aromatic heterocyclic group,

each R 1 and R 2 are the same or different, and are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C60 monovalent aromatic cyclic group, or a substituted or unsubstituted C3 to C60 monovalent aromatic heterocyclic group, or R 1 and R 2 are combined with each other to form one ring that is a pentagonal ring, a hexagonal ring, or a fused ring,

a is an integer ranging from 0 to 4,

b is an integer ranging from 0 to 3,

Z 1 to Z 8 are each independently a nitrogen atom or —CH═, and

W 1 to W 4 are each independently a halogen atom or a group represented by Chemical Formula 5-1

wherein, in Chemical Formula 5-1, R A to R D are each independently a C1 to C3 alkyl group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2019
From: TAKAHIRO, FUJIYAMA; KATO, FUMIAKI; MOTOYAMA, TAKAO; KONISHI, YUSAKU; ITO, MITSUNORI; KEIGO, FURUTA
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 047947/0811 →
Priority Claims (2)
JP 2018-002095 · Jan 10, 2018 · national
KR 10-2018-0070738 · Jun 20, 2018 · national
Continuity (1)
Related Publication 20190214566A1 · Jul 11, 2019
Cited By (1)
US 12,466,947