IP Library › Granted Patent US 10,308,735
Granted Patent B2
US 10,308,735 · App. 14/972,853 · Granted Jun 4, 2019

Material for organic light-emitting device and organic light-emitting device including the same

Inventors: Masashi Tsuji (Kanagawa, JP); Koji Hasegawa (Kanagawa, JP); Makoto Taguchi (Kanagawa, JP)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
C08F32/00H01L51/004H01L51/0043H01L51/0059H01L51/0067H01L51/0072H01L51/0085H01L51/5056
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Quick Facts
Patent No.
US 10,308,735
App. No.
14/972,853
Granted
Jun 4, 2019
Kind
B2
Abstract

A material for an organic light-emitting device, the material including a repeating unit represented by Formula 1: wherein, in Formula 1, R 1 , A, and X 1 are the same as described in the specification.

Claims (86)

1. A material for an organic light-emitting device, the material comprising

a repeating unit represented by Formula 1:

wherein, in Formula 1,

R 1 is selected from a single bond, a phenylene group, and a group represented by one of Formulae a1 to a9:

wherein, in Formulae a1 to a9,

R 22 is a C 1 -C 6 alkyl group,

X 21 and X 22 are each independently selected from an oxygen atom and a sulfur atom;

A is selected from an adamantylene group, a diadamantylene group, a triadamantylene group, and a tetraadamantylene group; and

X 1 is a charge transport unit represented by one of Formulae b1 to b13:

wherein, in Formulae b1 to b13,

R 311 , R 312 , R 313 , R 321 , R 322 , R 331 , R 341 , R 351 , R 352 , R 361 , R 362 , R 363 , R 371 , R 372 , R 381 , R 391 , R 3101 , R 3111 , R 3112 , R 3113 , R 3121 , R 3122 , R 3123 , R 3124 , R 3125 , R 3131 and R 3132 are each independently selected from a hydrogen atom, a C 1 -C 6 alkyl group, and a group represented by one of Formulae c1 to c16:

wherein, in Formulae c1 to c16,

p is 0 or 1; and

Z 11 , Z 12 , Z 21 , Z 31 , Z 41 , Z 42 , Z 51 , Z 52 , Z 53 , Z 61 , Z 62 , Z 71 , Z 72 , Z 81 , Z 82 , Z 91 , and Z 92 are each independently selected from a C 1 -C 6 alkyl group, a methoxy group, and a group represented by one of Formulae d1 to d7:

wherein, in Formulae d1 to d7,

alkyl indicates a C 1 -C 6 alkyl group;

Y 11 , Y 12 , Y 21 , Y 31 , Y 41 , Y 42 , Y 51 , Y 52 , Y 61 , Y 62 , and Y 63 are each independently a group represented by one of Formulae e1 to e11:

wherein, in Formulae e1 to e11,

R 411 , R 412 , R 421 , R 431 , R 441 , R 442 , R 451 , R 452 , R 461 , and R 462 are each independently selected from a hydrogen atom, a C 1 -C 6 alkyl group, a phenyl group, and a tolyl group.

2. The material of claim 1 , wherein

R 1 is selected from a phenylene group and a group represented by one of Formulae a1 to a9.

3. The material of claim 1 , wherein

R 1 is selected from a phenylene group and a group represented by Formula a1.

4. The material of claim 1 , wherein

R 1 is a phenylene group.

5. The material of claim 1 , wherein

X 1 is selected from an arylamine moiety, a fluorene moiety, a carbazole moiety, a dibenzofurane moiety, a dibenzothiophene moiety, each optionally forming a fused ring system or a spiro ring system; a fluorenone moiety, a quinone moiety, an anthraquinone moiety, a diphenylquinone moiety, a thiopyrandioxide moiety, an oxazole moiety, an oxadiazole moiety, a triazole moiety, an imidazole moiety, an anthrone moiety, a bipyridine moiety, and a phenanthroline moiety.

6. The material of claim 1 , wherein

X 1 is a group represented by one of Formulae b1 to b5, b8, and b11.

7. The material of claim 1 , wherein

X 1 is a group represented by one of Formulae b1 and b11.

8. The material of claim 1 , wherein

the repeating unit represented by Formula 1 is represented by Formula 1a:

wherein, in Formula 1a,

X 1 is the same as in Formula 1.

9. The material of claim 1 , wherein

the material for the organic light-emitting device comprises 20 to 500 repeating units in total.

10. The material of claim 1 , wherein

the material comprises the repeating unit represented by Formula 1 in an amount of 10 to 100 mol %.

11. The material of claim 1 , wherein

the material comprises the repeating unit represented by Formula 1 in an amount of 30 to 100 mol %.

12. The material of claim 1 , further comprising

a repeating unit represented by Formula 2:

wherein, in Formula 2,

R 10 is the same as R 1 in claim 1 ;

X 10 is the same as X 1 in claim 1 ; and

q is 0 or 1.

13. The material of claim 1 , wherein

the material for the organic light-emitting device is represented by Formula 3:

wherein, in Formula 3,

R 1 and R 10 are each independently defined as R 1 in Formula 1;

A is the same as A in Formula 1;

X 1 and X 10 are each independently defined as X 1 in Formula 1;

q is 0 or 1;

n is an integer of 20 to 500; and

m is an integer of 1 to 180.

14. The material of claim 13 , wherein

n and m satisfy the condition of 0.1≤n/(n+m)≤1.

15. The material of claim 13 , wherein

n and m satisfy the condition of 20≤n+m≤500.

16. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode;

wherein the organic layer comprises the material comprising:

a repeating unit represented by Formula 1:

wherein, in Formula 1,

R 1 is selected from a single bond, a phenylene group, and a group represented by one of Formulae a1 to a9:

wherein, in Formulae a1 to a9,

R 22 is a C 1 -C 6 alkyl group,

X 21 and X 22 are each independently selected from an oxygen atom and a sulfur atom;

A is selected from an adamantylene group, a diadamantylene group, a triadamantylene group, and a tetraadamantylene group; and

X 1 is a charge transport unit represented by one of Formulae b1 to b13:

wherein, in Formulae b1 to b13,

R 311 , R 312 , R 313 , R 321 , R 322 , R 331 , R 341 , R 351 , R 352 , R 361 , R 362 , R 363 , R 371 , R 372 , R 381 , R 391 , R 3101 , R 3111 , R 3112 , R 3113 , R 3121 , R 3122 , R 3123 , R 3124 ,R 3125 , R 3131 and R 3132 are each independently selected from a hydrogen atom, a C 1 -C 6 alkyl group, and a group represented by one of Formulae c1 to c16:

wherein, in Formulae c1 to c16,

p is 0 or 1; and

Z 11 , Z 12 , Z 21 , Z 31 , Z 41 , Z 42 , Z 51 , Z 52 , Z 53 , Z 61 , Z 62 , Z 71 , Z 72 , Z 81 , Z 82 , Z 91 , and Z 92 are each independently selected from a C 1 -C 6 alkyl group, a methoxy group, and a group represented by one of Formulae d1 to d7:

wherein, in Formulae d1 to d7,

alkyl indicates a C 1 -C 6 alkyl group;

Y 11 , Y 12 , Y 21 , Y 31 , Y 41 , Y 42 , Y 51 , Y 52 , Y 61 , Y 62 , and Y 63 are each independently a group represented by one of Formulae e1 to e11:

wherein, in Formulae e1 to e11,

R 411 , R 412 , R 421 , R 431 , R 441 , R 442 , R 451 , R 452 , R 461 , and R 462 are each independently selected from a hydrogen atom, a C 1 -C 6 alkyl group, a phenyl group, and a tolyl group.

17. The organic light-emitting device of claim 16 , wherein

the organic film comprises at least one layer selected from a hole injection layer and a hole transport layer; and

the at least one layer comprises the material.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 13, 2019
From: TSUJI, MASASHI; HASEGAWA, KOJI; TAGUCHI, MAKOTO
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 048317/0343 →
Priority Claims (2)
JP 2014-256674 · Dec 18, 2014 · national
KR 10-2015-0139993 · Oct 5, 2015 · national
Continuity (1)
Related Publication 20160181535A1 · Jun 23, 2016