IP Library › Granted Patent US 9,425,410

Granted Patent B2

US 9,425,410 · App. 13/940,187 · Granted Aug 23, 2016

Organic light-emitting diode

Inventors: So-Yeon Kim (Yongin, KR); Yoon-Hyun Kwak (Yongin, KR); Bum-Woo Park (Yongin, KR); Sun-Young Lee (Yongin, KR); Wha-Il Choi (Yongin, KR); Jong-Won Choi (Yongin, KR); Ji-Youn Lee (Yongin, KR)

Assignee: Samsung Display Co., Ltd.

H01L51/0072 H01L51/006 H01L51/0052 H01L51/0059 H01L51/0061 H01L51/0067 H01L51/0073 H01L51/0074 H01L51/0085 H01L51/5016 H01L51/5056

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Quick Facts

Patent No.: US 9,425,410
App. No.: 13/940,187
Granted: Aug 23, 2016
Kind: B2

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Abstract

An organic light-emitting diode includes a substrate, a first electrode on the substrate, a second electrode facing the first electrode, an emission layer between the first electrode and the second electrode, a hole transfer region between the first electrode and the emission layer, and an electron transfer region between the emission layer and the second electrode. The hole transfer region includes a first compound represented by Formula 1, and the emission layer includes a second compound represented by Formula 100.

Claims (165)

1. An organic light-emitting diode, comprising:

a substrate;

a first electrode on the substrate;

a second electrode facing the first electrode;

an emission layer between the first electrode and the second electrode;

a hole transfer region between the first electrode and the emission layer; and

an electron transfer region between the emission layer and the second electrode,

wherein the hole transfer region comprises a first compound represented by Formula 1, and the emission layer comprises a second compound represented by Formula 100A or 100B:

wherein, in Formula 1:

Ar 101 and Ar 102 are each independently a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, or a substituted or unsubstituted C 2 -C 60 heteroarylene group;

xa and xb are each independently an integer of 0 to 5;

R 101 and R 109 are each independently a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 2 -C 60 heteroaryl group;

R 102 to R 108 , and R 111 to R 119 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthiol group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, —N(Q 1 )(Q 2 ), or —Si(Q 3 )(Q 4 )(Q 5 ); and

Q 1 to Q 5 are each independently a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, or a C 2 -C 60 heteroaryl group; and

in Formula 100A and 100B:

X 1 is O or S;

Ring P and ring Q are each independently a substituted or unsubstituted C 3 -C 60 cyclic moiety, or a substituted or unsubstituted C 2 -C 60 heterocyclic moiety;

R 51 to R 60 are each independently a substituent represented by —(Ar 51 ) q —(Ar 61 );

Ar 51 is a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a C 2 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, or a substituted or unsubstituted C 2 -C 60 heteroarylene group;

Ar 61 is a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, —N(Q 21 )(Q 22 ), or —Si(Q 23 )(Q 24 )(Q 25 );

Q 21 and Q 22 are each independently a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 2 -C 60 heteroaryl group; and

Q 23 to Q 25 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 2 -C 60 heteroaryl group; and

q is an integer of 0 to 5,

provided that Ar 51 of R 57 in Formula 100B is a group represented by one of Formulae 103-4 to 103-10 and 103-14 to 103-16:

wherein, in Formulae 103-4 to 103-10 and 103-14 to 103-16:

Y 21 is O, S, or N(Z 43 );

Z 31 and Z 32 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group;

g1 is an integer of 1 to 5;

g3 is an integer of 1 to 3;

g4 is an integer of 1 to 4; and

g5 is 1 or 2.

2. The organic light-emitting diode of claim 1 , wherein Ar 101 and Ar 102 in Formula 1 are each independently a moiety represented by one of Formulae 3-1 to 3-24:

wherein, in Formulae 3-1 to 3-24:

Y 1 is O, S, C(R 21 )(R 22 ), or N(R 23 );

Z 1 , Z 2 , and R 21 to R 23 are each independently:

i) a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, or a C 1 -C 20 alkoxy group, or

ii) a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid group or a salt thereof, or

iii) a C 6 -C 20 aryl group or a C 2 -C 20 heteroaryl group, or

iv) a C 6 -C 20 aryl group or a C 2 -C 20 heteroaryl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group, or

v) —N(Q 11 )(Q 12 ), or —Si(Q 13 )(Q 14 )(Q 15 ), wherein Q 11 to Q 15 are each independently a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, or a C 2 -C 20 heteroaryl group;

d1 is an integer of 1 to 4;

d2 is an integer of 1 to 3;

d3 is an integer of 1 to 6;

d4 is an integer of 1 to 8; and

d5 is 1 or 2.

3. The organic light-emitting diode of claim 1 , wherein Ar 101 and Ar 102 in Formula 1 are each independently a moiety represented by one of Formulae 4-1 to 4-7:

4. The organic light-emitting diode of claim 1 , wherein, in Formula 1, either: i) xa=0 and xb=0; or ii) xa=1 and xb=0; or iii) xa=2 and xb=0; or iv) xa=0 and xb=1; or v) xa=0 and xb=2; or vi) xa=1 and xb=1.

5. The organic light-emitting diode of claim 1 , wherein, in Formula 1, R 101 and R 109 are each independently a moiety represented by one of Formulae 5-1 to 5-22:

wherein, in Formulae 5-1 to 5-22:

Y 2 and Y 3 are each independently O, S, C(R 25 )(R 26 ), or N(R 27 );

Z 11 to Z 14 , and R 25 to R 27 are each independently:

iii) a C 6 -C 20 aryl group or a C 2 -C 20 heteroaryl group, or

iv) a C 6 -C 20 aryl group or a C 2 -C 20 heteroaryl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 an alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group, or

e1 is an integer of 1 to 5;

e2 is an integer of 1 to 7;

e3 is an integer of 1 to 3;

e4 is an integer of 1 to 4; and

e5 is 1 or 2.

6. The organic light-emitting diode of claim 1 , wherein R 101 in Formula 1 is represented by one of Formulae 6-1 to 6-8, and R 109 in Formula 1 is represented by one of Formulae 6-1 to 6-11:

wherein, in Formulae 6-1 to 6-11:

Z 11a to Z 11c , R 25 , and R 26 are each independently:

i) a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, or a C 1 -C 20 alkoxy group, or

iii) a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group, or

iv) a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group; and

each Q 12 is each independently a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group.

7. The organic light-emitting diode of claim 1 , wherein R 111 and R 112 in Formula 1 are each independently:

i) a C 1 -C 20 alkyl group, or

ii) a C 1 -C 20 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid group or a salt thereof, or

8. The organic light-emitting diode of claim 1 , wherein the

ring P and the ring Q are each independently:

i) benzene, naphthalene, fluorene, carbazole, dibenzofuran, or dibenzothiophene; or

ii) benzene, naphthalene, fluorene, carbazole, dibenzofuran, or dibenzothiophene substituted with at least one of:

ii)a) a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, or a C 1 -C 20 alkoxy group, or

ii)b) a C 1 -C 20 alkyl group, or a C 1 -C 60 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid group or a salt thereof, or

ii)c) a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group, or

ii)d) a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group, or

ii)e) —N(Q 11 )(Q 12 ), wherein Q 11 and Q 12 are each independently a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group.

9. The organic light-emitting diode of claim 1 , wherein the second compound is represented by one of Formulae 100A-1 to 100A-8 and 100B-1 to 100B-8:

wherein, in Formulae 100A-1 to 100A-8 and 100B-1 to 100B-8:

X 12 is O, S, C(R 71 )(R 72 ), or N(R 73 );

R 61 , R 62 , and R 71 to R 73 are each independently:

ii) a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid group or a salt thereof, or

iii) a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, or a C 2 -C 60 heteroaryl group, or

iv) a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, or a C 2 -C 60 heteroaryl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or a isoquinolyl group, or

v) —N(Q 11 )(Q 12 ), or —Si(Q 13 )(Q 14 )(Q 15 ), wherein Q 11 and Q 12 are each independently a C 6 -C 60 aryl group or a C 2 -C 60 heteroaryl group, and Q 13 to Q 15 are each independently a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, or a C 2 -C 60 heteroaryl group;

r1 is an integer of 1 to 4;

r2 is 1 or 2; and

r3 is an integer of 1 to 6.

10. The organic light-emitting diode of claim 1 , wherein Ar 51 in Formula 100A and 100B is:

i) a phenylene group, a naphthalene group, a fluorenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, a carbazolylene group, a triazinylene group, a dibenzofuranylene group, or a dibenzothiophenylene group, or

ii) a phenylene group, a naphthalene group, a fluorenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, a carbazolylene group, a triazinylene group, a dibenzofuranylene group, or a dibenzothiophenylene group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group.

11. The organic light-emitting diode of claim 1 , wherein Ar 61 of R 56 , R 57 , R 58 and R 59 in Formula 100A and 100B is a group represented by one of Formulae 103-1 to 103-16:

wherein, in Formulae 103-1 to 103-16:

Y 21 is O, S, C(Z 41 )(Z 42 ), or N(Z 43 );

Z 31 , Z 32 , and Z 41 to Z 43 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group;

Q 21 and Q 22 are each independently a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group;

g1 is an integer of 1 to 5;

g2 is an integer of 1 to 7;

g3 is an integer of 1 to 3;

g4 is an integer of 1 to 4; and

g5 is 1 or 2.

12. An organic light-emitting diode, comprising:

a substrate;

a first electrode on the substrate;

a second electrode facing the first electrode;

an emission layer between the first electrode and the second electrode;

a hole transfer region between the first electrode and the emission layer; and

an electron transfer region between the emission layer and the second electrode,

wherein the hole transfer region comprises a first compound represented by Formula 1, and the emission layer comprises a second compound represented by Formula 100A-H1, 100A-H2, 100B-H1, or 100B-H2:

Formula 1

wherein, in Formula 1:

xa and xb are each independently an integer of 0 to 5;

R 102 to R 108 and R 111 to R 119 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthiol group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, —N(Q 1 )(Q 2 ), or —Si(Q 3 )(Q 4 )(Q 5 ); and

Q 1 to Q 5 are each independently a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, or a C 2 -C 60 heteroaryl group;

wherein, in Formulae 100A-H1, 100A-H2, 100B-H1, and 100B-H2:

X 1 is O or S;

ring P and ring Q are each independently:

i) benzene, naphthalene, fluorene, carbazole, dibenzofuran, or dibenzothiophene; or

ii) benzene, naphthalene, fluorene, carbazole, dibenzofuran, or dibenzothiophene substituted with at least one of:

wherein Q 11 and Q 12 are each independently a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group;

R 55 , R 56 , R 59 , R 60 , Z 21 , and Z 22 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group;

f1 and f2 are each independently 0, 1, or 2; and

Ar 61 is a group represented by one of Formulae 103-1 to 103-16:

wherein, in Formulae 103-1 to 103-16:

Y 21 is O, S, C(Z 41 )(Z 42 ), Or N(Z 43 );

g1 is an integer of 1 to 5;

g2 is an integer of 1 to 7;

g3 is an integer of 1 to 3;

g4 is an integer of 1 to 4; and

g5 is 1 or 2.

13. The organic light-emitting diode of claim 1 , wherein the first compound is one of Compounds 1-1 to 1-19:

14. An organic light-emitting diode, comprising:

a substrate;

a first electrode on the substrate;

a second electrode facing the first electrode;

an emission layer between the first electrode and the second electrode;

a hole transfer region between the first electrode and the emission layer; and

an electron transfer region between the emission layer and the second electrode,

wherein the hole transfer region comprises a first compound represented by Formula 1, and the emission layer comprises a second compound selected from the group consisting of Compounds 2-1 through 2-25:

Formula 1

wherein, in Formula 1:

xa and xb are each independently an integer of 0 to 5;

Q 1 to Q 5 are each independently a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, or a C 2 -C 60 heteroaryl group;

15. The organic light-emitting diode of claim 1 , wherein the hole transfer region further comprises a charge-generating material.

16. The organic light-emitting diode of claim 1 , wherein the hole transfer region comprises a hole transport layer, and the first compound is in the hole transport layer.

17. The organic light-emitting diode of claim 16 , wherein the hole transfer region further comprises at least one of a hole injection layer between the first electrode and the hole transport layer, and a buffer layer between the hole transport layer and the emission layer.

18. The organic light-emitting diode of claim 1 , wherein the hole transfer region is a single layer.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2013

From: KIM, SO-YEON; KWAK, YOON-HYUN; PARK, BUM-WOO; LEE, SUN-YOUNG; CHOI, WHA-IL; CHOI, JONG-WON; LEE, JI-YOUN

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 030791/0304 →

Priority Claims (1)

KR 10-2013-0015534 · Feb 13, 2013 · national

Continuity (1)

Related Publication 20140225072A1 · Aug 14, 2014